Chemistry › Organic Chemistry

Organophosphorus compounds synthesis

Works Count: 58337

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This cluster of papers covers the chemistry, synthesis, and applications of phosphonates, with a focus on organophosphorus synthesis, enantioselective synthesis, biological activity, catalytic reactions, medicinal chemistry, asymmetric hydrophosphonylation, metal-catalyzed reactions, oxidative stress mechanisms, and aminophosphonic acids.

Keywords

Phosphonate Chemistry; Organophosphorus Synthesis; Enantioselective Synthesis; Biological Activity; Catalytic Reactions; Medicinal Chemistry; Asymmetric Hydrophosphonylation; Metal-Catalyzed Reactions; Oxidative Stress Mechanisms; Aminophosphonic Acids

Phosphorus in organic synthesis—VII

1974-01-01

Kunihiro Ninomiya , Takayuki Shioiri , Susumu Yamada

ENZYMATIC ESTERIFICATION OF α-GLYCEROPHOSPHATE BY LONG CHAIN FATTY ACIDS

1953-09-01

Arthur Kornberg , W.E. Pricer

Chemistry of the amino acids

1961-01-01

Jesse P. Greenstein , Milton Winitz

Aminophosphonic and aminophosphinic acids : chemistry and biological activity

2000-01-01

Harry R. Hudson , Valery P. Kukhar

Naturally Occurring Aminophosphonic and Aminophosphinic Acids (P. Mastalerz & P. Kafarski) Synthesis of -Aminoalkanephosphinic Acids (P. Kafarski & J. Zo ) Synthesis of Aminoalkanephosphonic and Aminoalkanephosphinic Acids with the Amino … Naturally Occurring Aminophosphonic and Aminophosphinic Acids (P. Mastalerz & P. Kafarski) Synthesis of -Aminoalkanephosphinic Acids (P. Kafarski & J. Zo ) Synthesis of Aminoalkanephosphonic and Aminoalkanephosphinic Acids with the Amino Substituent in Other than the -Position (V. Kukhar) -Amino Acid Analogues Bearing Side-Chain C-P Linkages (S. Lall and R. Engel) Asymmetric Synthesis of Aminophosphonic and Aminophosphinic Acids (V. Kukhar) Synthesis of Phosphono- and Phosphinopeptides (P. Kafarski & B. Lejczak) Column Chromatography of Aminophosphonic Acids and Phosphonopeptides (S. Galushko) Physical Properties and NMR-Spectroscopic Characterization of Aminophosphonates and Aminophosphinates (G. Hdgele) Structure and Stability Constants of Metal Complexes in Solution (T. Kiss & I. Lazar) X-Ray Crystallographic Studies (N. Choi & M. McPartlin) Mass Spectrometry and Gas Chromatography-Mass Spectrometry of Aminoalkanephosphonic Acids (Z. Kudzin & M. Sochaki) The Biological Activity of Phosphono- and Phosphinopeptides (P. Kafarski & B. Lejezak) Aminophosphonic and Aminophosphinic Acids and their Derivatives as Agrochemicals (H. Hudson) Neuroactive Aminophosphonic and Aminophosphinic Acid Derivatives (D. Jane) Aminophosphonic and Aminophosphinic Acid Derivatives in the Design of Transition State Analogue Inhibitors: Biomedical Opportunities and Limitations (J. Oleksyszyn) Aminophosphonic and Aminophosphinic Acids in the Design and Synthesis of HIV Protease Inhibitors (A. Peyman) Aminophosphonic Acid Derivatives as Antithrombotic Agents (D. Green, et al.) Aminophosphonic and Aminophosphinic Acid Derivatives as Inhibitors of Human Collagenase (R. Markwell) Index.

The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects

1989-06-01

Bruce E. Maryanoff , Allen B. Reitz

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspectsBruce E. Maryanoff and Allen B. ReitzCite this: Chem. Rev. 1989, 89, 4, … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspectsBruce E. Maryanoff and Allen B. ReitzCite this: Chem. Rev. 1989, 89, 4, 863–927Publication Date (Print):June 1, 1989Publication History Published online1 May 2002Published inissue 1 June 1989https://doi.org/10.1021/cr00094a007RIGHTS & PERMISSIONSArticle Views26883Altmetric-Citations2157LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (9 MB) Get e-Alerts Get e-Alerts

Modern organoselenium chemistry

1978-01-01

Derrick L. J. Clive

The infra-red spectra of some inorganic phosphorus compounds

1954-01-01

D. E. C. Corbridge , E. J. Lowe

The first page of this article is displayed as the abstract. The first page of this article is displayed as the abstract.

Phosphorus-31 NMR spectroscopy in stereochemical analysis

1989-01-01

J. G. Verkade , Louis D. Quin , S.L. Jones

Palladium-catalyzed New Carbon-Phosphorus Bond Formation

1982-03-01

Toshikazu Hirao , Toshio Masunaga , Naoto Yamada +2 more

Abstract Dialkyl arylphosphonates are prepared by the palladium-catalyzed reaction of aryl bromides with dialkyl phosphite in the presence of triethylamine. The similar treatment of vinyl bromides gives dialkyl vinylphosphonates stereoselectively. Abstract Dialkyl arylphosphonates are prepared by the palladium-catalyzed reaction of aryl bromides with dialkyl phosphite in the presence of triethylamine. The similar treatment of vinyl bromides gives dialkyl vinylphosphonates stereoselectively.

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Analogous .alpha.,.alpha.'-bis-carbenoid, triply bonded species: synthesis of a stable .lambda.3-phosphino carbene-.lambda.5-phosphaacetylene

1988-09-01

Alain Igau , Hansjörg Grützmacher , Antoine Baceiredo +1 more

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAnalogous .alpha.,.alpha.'-bis-carbenoid, triply bonded species: synthesis of a stable .lambda.3-phosphino carbene-.lambda.5-phosphaacetyleneAlain. Igau, Hansjorg. Grutzmacher, Antoine. Baceiredo, and Guy. BertrandCite this: J. Am. Chem. Soc. 1988, 110, 19, … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAnalogous .alpha.,.alpha.'-bis-carbenoid, triply bonded species: synthesis of a stable .lambda.3-phosphino carbene-.lambda.5-phosphaacetyleneAlain. Igau, Hansjorg. Grutzmacher, Antoine. Baceiredo, and Guy. BertrandCite this: J. Am. Chem. Soc. 1988, 110, 19, 6463–6466Publication Date (Print):September 1, 1988Publication History Published online1 May 2002Published inissue 1 September 1988https://pubs.acs.org/doi/10.1021/ja00227a028https://doi.org/10.1021/ja00227a028research-articleACS PublicationsRequest reuse permissionsArticle Views6810Altmetric-Citations747LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

BIOLOGICAL ACTIVITY OF AMINOPHOSPHONIC ACIDS

1991-11-01

Paweł Kafarski , Barbara Lejczak

Abstract Aminophosphonates are analogues of amino acids in which a carboxylic moiety is replaced by phosphonic acid or related groups. Acting as antagonists of amino acids, they inhibit enzymes involved … Abstract Aminophosphonates are analogues of amino acids in which a carboxylic moiety is replaced by phosphonic acid or related groups. Acting as antagonists of amino acids, they inhibit enzymes involved in amino acid metabolism and thus affect the physiological activity of the cell. These effects may be exerted as antibacterial, plant growth regulatory or neuromodulatory. Chosen representative examples of biologically active aminophosphonates are presented in some detail.

Rapid and efficient synthesis of nucleoside 5'-0-(1-thiotriphosphates), 5'-triphosphates and 2',3'-cyclophosphorothioates using 2-chloro-4H-1,3,2-benzodioxaphosphorin-4-one

1989-02-01

János Ludwig , Fritz Eckstein

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTRapid and efficient synthesis of nucleoside 5'-0-(1-thiotriphosphates), 5'-triphosphates and 2',3'-cyclophosphorothioates using 2-chloro-4H-1,3,2-benzodioxaphosphorin-4-oneJanos Ludwig and Fritz EcksteinCite this: J. Org. Chem. 1989, 54, 3, 631–635Publication Date (Print):February 1, … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTRapid and efficient synthesis of nucleoside 5'-0-(1-thiotriphosphates), 5'-triphosphates and 2',3'-cyclophosphorothioates using 2-chloro-4H-1,3,2-benzodioxaphosphorin-4-oneJanos Ludwig and Fritz EcksteinCite this: J. Org. Chem. 1989, 54, 3, 631–635Publication Date (Print):February 1, 1989Publication History Published online1 May 2002Published inissue 1 February 1989https://pubs.acs.org/doi/10.1021/jo00264a024https://doi.org/10.1021/jo00264a024research-articleACS PublicationsRequest reuse permissionsArticle Views3866Altmetric-Citations319LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Olefin synthesis with organic phosphonate carbanions

1974-02-01

John Boutagy , Richard Thomas

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTOlefin synthesis with organic phosphonate carbanionsJohn Boutagy and Richard ThomasCite this: Chem. Rev. 1974, 74, 1, 87–99Publication Date (Print):February 1, 1974Publication History Published online1 May 2002Published inissue … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTOlefin synthesis with organic phosphonate carbanionsJohn Boutagy and Richard ThomasCite this: Chem. Rev. 1974, 74, 1, 87–99Publication Date (Print):February 1, 1974Publication History Published online1 May 2002Published inissue 1 February 1974https://pubs.acs.org/doi/10.1021/cr60287a005https://doi.org/10.1021/cr60287a005research-articleACS PublicationsRequest reuse permissionsArticle Views5132Altmetric-Citations537LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

The Direct Synthesis of α-Aminomethylphosphonic Acids. Mannich-Type Reactions with Orthophosphorous Acid

1966-05-01

Kurt Moedritzer , R. R. Irani

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Direct Synthesis of α-Aminomethylphosphonic Acids. Mannich-Type Reactions with Orthophosphorous AcidKurt Moedritzer and Riyad R. IraniCite this: J. Org. Chem. 1966, 31, 5, 1603–1607Publication Date (Print):May 1, … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Direct Synthesis of α-Aminomethylphosphonic Acids. Mannich-Type Reactions with Orthophosphorous AcidKurt Moedritzer and Riyad R. IraniCite this: J. Org. Chem. 1966, 31, 5, 1603–1607Publication Date (Print):May 1, 1966Publication History Published online1 May 2002Published inissue 1 May 1966https://pubs.acs.org/doi/10.1021/jo01343a067https://doi.org/10.1021/jo01343a067research-articleACS PublicationsRequest reuse permissionsArticle Views3676Altmetric-Citations417LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Chemistry of bis(diphenylphosphino)methane

1983-01-01

Richard J. Puddephatt

R. J. Puddephatt, Chem. Soc. Rev., 1983, 12, 99 DOI: 10.1039/CS9831200099 R. J. Puddephatt, Chem. Soc. Rev., 1983, 12, 99 DOI: 10.1039/CS9831200099

Fluorinated Phosphonates: Synthesis and Biomedical Application

2006-07-20

V. D. ROMANENKO , Valery P. Kukhar

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTFluorinated Phosphonates: Synthesis and Biomedical ApplicationVadim D. Romanenko and Valery P. KukharView Author Information Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of the Ukraine, … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTFluorinated Phosphonates: Synthesis and Biomedical ApplicationVadim D. Romanenko and Valery P. KukharView Author Information Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of the Ukraine, 1 Murmanska Street, Kyiv-94 02660, Ukraine Cite this: Chem. Rev. 2006, 106, 9, 3868–3935Publication Date (Web):July 20, 2006Publication History Received20 January 2006Published online20 July 2006Published inissue 1 September 2006https://pubs.acs.org/doi/10.1021/cr051000qhttps://doi.org/10.1021/cr051000qresearch-articleACS PublicationsCopyright © 2006 American Chemical SocietyRequest reuse permissionsArticle Views6273Altmetric-Citations316LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Anions,Chemical reactions,Organophosphorus compounds,Peptides and proteins,Reaction products Get e-Alerts

A Tertiary Phosphine-catalyzed Reaction of Acrylic Compounds with Aldehydes

1968-11-01

Kenichi Morita , Zennosuke Suzuki , Hiromitsu Hirose

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Aminophosphonic Acids of Potential Medical Importance

2001-11-01

Paweł Kafarski , Barbara Lejczak

Aminophosphonic acids were almost unknown in 1959 but today they are the subject of more than 6000 papers. Their negligible mammalian toxicity, and the fact that they very efficiently mimic … Aminophosphonic acids were almost unknown in 1959 but today they are the subject of more than 6000 papers. Their negligible mammalian toxicity, and the fact that they very efficiently mimic aminocarboxylic acids makes them extremely important antimetabolites, which compete with their carboxylic counterparts for the active sites of enzymes and other cell receptors. Although biological importance of these compounds was recognized over 50 years ago they still represent promising and somewhat undiscovered class of potential drugs.

Bioisosterism: A Useful Strategy for Molecular Modification and Drug Design

2005-01-01

Lı́dia Moreira Lima , Eliezer J. Barreiro

This review aim to demonstrate the role of bioisosterism in rational drug design as well as in the molecular modification and optimization process aiming to improve pharmacodynamic and pharmacokinetic properties … This review aim to demonstrate the role of bioisosterism in rational drug design as well as in the molecular modification and optimization process aiming to improve pharmacodynamic and pharmacokinetic properties of lead compounds. Keywords: lead compound, isosterism, antagonist, pharmacodynamic, pharmacokinetic, hplc, prostaglandin-h synthase-2 (pghs-

1077. The rôle of 3d-orbitals in π-bonds between (a) silicon, phosphorus, sulphur, or chlorine and (b) oxygen or nitrogen

1961-01-01

D. W. J. Cruickshank

D. W. J. Cruickshank, J. Chem. Soc., 1961, 5486 DOI: 10.1039/JR9610005486 D. W. J. Cruickshank, J. Chem. Soc., 1961, 5486 DOI: 10.1039/JR9610005486

Stoffwechselprodukte von Mikroorganismen. 98. Mitteilung. Phosphinothricin und Phosphinothricyl‐Alanyl‐Alanin

1972-01-31

E. Bayer , K. H. Gugel , K. Hägele +4 more

Abstract From cultures of Streptomyces viridochromogenes a new antibiotic, phosphinothricylalanyl‐alanine, has been isolated. The new amino acid phosphinothricin is 2‐amino‐4‐methyl‐phosphino‐butyric acid, its structure is confirmed by synthesis. The tripeptide is … Abstract From cultures of Streptomyces viridochromogenes a new antibiotic, phosphinothricylalanyl‐alanine, has been isolated. The new amino acid phosphinothricin is 2‐amino‐4‐methyl‐phosphino‐butyric acid, its structure is confirmed by synthesis. The tripeptide is highly active against Gram ‐positive and Gram ‐negative bacteria and against the fungus Botrytis cinerea . Phosphinothricin is an active glutamine synthetase inhibitor.

Histochemical Comparison of Naphthol AS-Phosphates for the Demonstration of Phosphatases

1958-03-01

M. S. Burstone

Journal Article Histochemical Comparison of Naphthol AS-Phosphates for the Demonstration of Phosphatases Get access M. S. Burstone M. S. Burstone National Institute of Dental Research,3Bethesda, Maryland Search for other works … Journal Article Histochemical Comparison of Naphthol AS-Phosphates for the Demonstration of Phosphatases Get access M. S. Burstone M. S. Burstone National Institute of Dental Research,3Bethesda, Maryland Search for other works by this author on: Oxford Academic PubMed Google Scholar JNCI: Journal of the National Cancer Institute, Volume 20, Issue 3, March 1958, Pages 601–615, https://doi.org/10.1093/jnci/20.3.601 Published: 01 March 1958 Article history Received: 23 September 1957 Published: 01 March 1958

1-Aminoalkylphosphonous acids. Part 1. Isosteres of the protein amino acids

1984-01-01

E. K. Baylis , Colin D. Campbell , John G. Dingwall

The synthesis of 1-aminoalkylphosphonous acids, isosteres of the protein amino acids, by addition of hypophosphorous acid to diphenylmethylimines is described. These analogues of glycine, alanine, valine, leucine, isoleucine, phenylalanine, tyrqsine, … The synthesis of 1-aminoalkylphosphonous acids, isosteres of the protein amino acids, by addition of hypophosphorous acid to diphenylmethylimines is described. These analogues of glycine, alanine, valine, leucine, isoleucine, phenylalanine, tyrqsine, tryptophan, serine, threonine, methionine, cysteine, cystine, glutamic acid, lysine, ornithine, arginine, and proline have been prepared and the analogues of alanine, valine, leucine, phenylalanine, and methionine resolved. Tha alanine, valine and methionine analogues have interesting antimicrobial activity and the alanine analogue has plant growth inhibiting properties. Oxidation of the appropriate 1-aminoalkylphosphonous acids gave the 1-aminoalkyl-phosphonic acid analogues of (±)-alanine, (–)-alanine, (±)-valine, (–)-valine, (±)-serine, (±)-threonine, (±)-lysine, (–)-leucine, and (±)-ornithine.

2-Cyanoethyl Phosphate and its Use in the Synthesis of Phosphate Esters1

1961-01-01

G. M. Tener

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXT2-Cyanoethyl Phosphate and its Use in the Synthesis of Phosphate Esters1G. M. TenerCite this: J. Am. Chem. Soc. 1961, 83, 1, 159–168Publication Date (Print):January 1, 1961Publication History … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXT2-Cyanoethyl Phosphate and its Use in the Synthesis of Phosphate Esters1G. M. TenerCite this: J. Am. Chem. Soc. 1961, 83, 1, 159–168Publication Date (Print):January 1, 1961Publication History Published online1 May 2002Published inissue 1 January 1961https://pubs.acs.org/doi/10.1021/ja01462a032https://doi.org/10.1021/ja01462a032research-articleACS PublicationsRequest reuse permissionsArticle Views1876Altmetric-Citations367LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Synthesis of High Polymeric Alkoxy- and Aryloxyphosphonitriles

1965-09-01

Harry R. Allcock , R. L. Kugel

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of High Polymeric Alkoxy- and AryloxyphosphonitrilesH. R. Allcock and R. L. KugelCite this: J. Am. Chem. Soc. 1965, 87, 18, 4216–4217Publication Date (Print):September 1, 1965Publication History … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of High Polymeric Alkoxy- and AryloxyphosphonitrilesH. R. Allcock and R. L. KugelCite this: J. Am. Chem. Soc. 1965, 87, 18, 4216–4217Publication Date (Print):September 1, 1965Publication History Published online1 May 2002Published inissue 1 September 1965https://pubs.acs.org/doi/10.1021/ja01096a056https://doi.org/10.1021/ja01096a056research-articleACS PublicationsRequest reuse permissionsArticle Views1868Altmetric-Citations423LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Remarkable Potential of the α-Aminophosphonate/Phosphinate Structural Motif in Medicinal Chemistry

2011-07-22

Artur Mucha , Paweł Kafarski , Łukasz Berlicki

ADVERTISEMENT RETURN TO ISSUEPerspectiveNEXTRemarkable Potential of the α-Aminophosphonate/Phosphinate Structural Motif in Medicinal ChemistryArtur Mucha, Paweł Kafarski, and Łukasz Berlicki*View Author Information Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University … ADVERTISEMENT RETURN TO ISSUEPerspectiveNEXTRemarkable Potential of the α-Aminophosphonate/Phosphinate Structural Motif in Medicinal ChemistryArtur Mucha, Paweł Kafarski, and Łukasz Berlicki*View Author Information Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, PolandPhone: +48-71-320-4080. Fax: +48-71-320-2427. E-mail: [email protected]Cite this: J. Med. Chem. 2011, 54, 17, 5955–5980Publication Date (Web):July 22, 2011Publication History Received11 May 2011Published online5 August 2011Published inissue 8 September 2011https://pubs.acs.org/doi/10.1021/jm200587fhttps://doi.org/10.1021/jm200587freview-articleACS PublicationsCopyright © 2011 American Chemical SocietyRequest reuse permissionsArticle Views7862Altmetric-Citations518LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Chemical structure,Inhibitors,Monomers,Organophosphorus compounds,Peptides and proteins Get e-Alerts

The Utility of Phosphonate Carbanions in Olefin Synthesis

1961-04-01

William S. Wadsworth , William D. Emmons

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Utility of Phosphonate Carbanions in Olefin SynthesisWilliam S. Wadsworth and William D. EmmonsCite this: J. Am. Chem. Soc. 1961, 83, 7, 1733–1738Publication Date (Print):April 1, 1961Publication … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Utility of Phosphonate Carbanions in Olefin SynthesisWilliam S. Wadsworth and William D. EmmonsCite this: J. Am. Chem. Soc. 1961, 83, 7, 1733–1738Publication Date (Print):April 1, 1961Publication History Published online1 May 2002Published inissue 1 April 1961https://pubs.acs.org/doi/10.1021/ja01468a042https://doi.org/10.1021/ja01468a042research-articleACS PublicationsRequest reuse permissionsArticle Views9150Altmetric-Citations1217LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Nucleoside Polyphosphates. X.1 The Synthesis and Some Reactions of Nucleoside-5' Phosphoromorpholidates and Related Compounds. Improved Methods for the Preparation of Nucleoside-5' Polyphosphates1

1961-02-01

J. G. Moffatt , H. G. Khorana

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNucleoside Polyphosphates. X.1 The Synthesis and Some Reactions of Nucleoside-5' Phosphoromorpholidates and Related Compounds. Improved Methods for the Preparation of Nucleoside-5' Polyphosphates1J. G. Moffatt and H. G. … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNucleoside Polyphosphates. X.1 The Synthesis and Some Reactions of Nucleoside-5' Phosphoromorpholidates and Related Compounds. Improved Methods for the Preparation of Nucleoside-5' Polyphosphates1J. G. Moffatt and H. G. KhoranaCite this: J. Am. Chem. Soc. 1961, 83, 3, 649–658Publication Date (Print):February 1, 1961Publication History Published online1 May 2002Published inissue 1 February 1961https://pubs.acs.org/doi/10.1021/ja01464a034https://doi.org/10.1021/ja01464a034research-articleACS PublicationsRequest reuse permissionsArticle Views1878Altmetric-Citations389LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Phosphinemethylenes.1 II. Triphenylphosphineacylmethylenes

1957-01-01

Fausto Ramírez , Samuel Dershowitz

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPhosphinemethylenes.1 II. TriphenylphosphineacylmethylenesFAUSTO RAMIREZ and SAMUEL DERSHOWITZCite this: J. Org. Chem. 1957, 22, 1, 41–45Publication Date (Print):January 1, 1957Publication History Published online1 May 2002Published inissue 1 January … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPhosphinemethylenes.1 II. TriphenylphosphineacylmethylenesFAUSTO RAMIREZ and SAMUEL DERSHOWITZCite this: J. Org. Chem. 1957, 22, 1, 41–45Publication Date (Print):January 1, 1957Publication History Published online1 May 2002Published inissue 1 January 1957https://pubs.acs.org/doi/10.1021/jo01352a010https://doi.org/10.1021/jo01352a010research-articleACS PublicationsRequest reuse permissionsArticle Views1161Altmetric-Citations348LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Review on Modern Advances of Chemical Methods for the Introduction of a Phosphonic Acid Group

2011-10-19

Charles S. Demmer , Niels Krogsgaard‐Larsen , Lennart Bunch

ADVERTISEMENT RETURN TO ISSUEPREVReviewReview on Modern Advances of Chemical Methods for the Introduction of a Phosphonic Acid GroupCharles S. Demmer, Niels Krogsgaard-Larsen, and Lennart Bunch*View Author Information Department of Medicinal … ADVERTISEMENT RETURN TO ISSUEPREVReviewReview on Modern Advances of Chemical Methods for the Introduction of a Phosphonic Acid GroupCharles S. Demmer, Niels Krogsgaard-Larsen, and Lennart Bunch*View Author Information Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Copenhagen, Universitetsparken 2, DK-2100 Copenhagen, DenmarkPhone: +45 35336244. Fax: +45 35336041. E-mail: [email protected]Cite this: Chem. Rev. 2011, 111, 12, 7981–8006Publication Date (Web):October 19, 2011Publication History Received15 July 2011Published online19 October 2011Published inissue 14 December 2011https://pubs.acs.org/doi/10.1021/cr2002646https://doi.org/10.1021/cr2002646review-articleACS PublicationsCopyright © 2011 American Chemical SocietyRequest reuse permissionsArticle Views12566Altmetric-Citations459LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Alkyls,Catalysts,Hydrocarbons,Organophosphorus compounds,Reagents Get e-Alerts

The Synthesis of Esters of Substituted Amino Phosphonic Acids1a

1952-03-01

Ellis K. Fields

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Synthesis of Esters of Substituted Amino Phosphonic Acids1aEllis K. FieldsCite this: J. Am. Chem. Soc. 1952, 74, 6, 1528–1531Publication Date (Print):March 1, 1952Publication History Published online1 … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Synthesis of Esters of Substituted Amino Phosphonic Acids1aEllis K. FieldsCite this: J. Am. Chem. Soc. 1952, 74, 6, 1528–1531Publication Date (Print):March 1, 1952Publication History Published online1 May 2002Published inissue 1 March 1952https://pubs.acs.org/doi/10.1021/ja01126a054https://doi.org/10.1021/ja01126a054research-articleACS PublicationsRequest reuse permissionsArticle Views2255Altmetric-Citations493LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Phosphinate Chemistry in the 21st Century: A Viable Alternative to the Use of Phosphorus Trichloride in Organophosphorus Synthesis.

2013-08-02

Jean‐Luc Montchamp

Organophosphorus compounds are important in everyday applications ranging from agriculture to medicine and are used in flame retardants and other materials. Although organophosphorus chemistry is known as a mature and … Organophosphorus compounds are important in everyday applications ranging from agriculture to medicine and are used in flame retardants and other materials. Although organophosphorus chemistry is known as a mature and specialized area, researchers would like to develop new methods for synthesizing organophosphorus compounds to improve the safety and sustainability of these chemical processes. The vast majority of compounds that contain a phosphorus-carbon bond are manufactured using phosphorus trichloride (PCl3) as an intermediate. However, these reactions require chlorine, and researchers would like to avoid the use of PCl3 and develop safer chemistry that also decreases energy consumption and minimizes waste. Researchers have already proposed and discussed two primary strategies based on elemental phosphorus (P4 or Pred) or on phosphine (PH3) as alternatives to PCl3. However, phosphinates, an important class of phosphorus compounds defined as any compound with a phosphorus atom attached to two oxygens, R(1)R(2)P(O)(OR) (R(1)/R(2) = hydrogen/carbon), offer another option. This Account discusses the previously neglected potential of these phosphinates as replacements of PCl3 for the preparation of organophosphorus compounds. Because of their strong reductive properties, industry currently uses the simplest members of this class of compounds, hypophosphites, for one major application: electroless plating. In comparison with other proposed PCl3 surrogates, hypophosphorous derivatives can offer improved stability, lower toxicity, higher solubility, and increased atom economy. When their reducing power is harnessed to form phosphorus-carbon or phosphorus-oxygen bonds, these compounds are also rich and versatile precursors to organophosphorus compounds. This Account examines the use of transition metal-catalyzed reactions such as cross-coupling and hydrophosphinylation for phosphorus-carbon bond formation. Because the most important industrial organophosphorus compounds include compounds triply or quadruply bound to oxygen, I also discuss controlled transfer hydrogenation for phosphorus-oxygen bond formation. I hope that this Account will further promote research in this novel and exciting yet much underdeveloped area of phosphinate activation.

Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid

1986-01-01

F. R. Atherton , Cedric H. Hassall , Robert Lambert

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acidFrank R. Atherton, Cedric H. Hassall, and Robert W. LambertCite this: J. Med. Chem. 1986, … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acidFrank R. Atherton, Cedric H. Hassall, and Robert W. LambertCite this: J. Med. Chem. 1986, 29, 1, 29–40Publication Date (Print):January 1, 1986Publication History Published online1 May 2002Published inissue 1 January 1986https://pubs.acs.org/doi/10.1021/jm00151a005https://doi.org/10.1021/jm00151a005research-articleACS PublicationsRequest reuse permissionsArticle Views1873Altmetric-Citations513LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

The Chemistry of Organophosphorus Compounds

1990-07-25

Multiple Bonds and Low Coordination in Phosphorus Chemistry

1991-11-01

John F. Nixon

Organic Phosphorus Compounds

1973-08-01

Dietmar Seyferth

The aza-Wittig reaction: an efficient tool for the construction of carbon–nitrogen double bonds

2006-11-02

Francisco Palácios , Concepción Alonso , Domitila Aparicio +2 more

Regio- and stereochemical control in substitution reactions of cyclophosphazenes

1991-03-01

Christopher W. Allen

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTRegio- and stereochemical control in substitution reactions of cyclophosphazenesChristopher W. AllenCite this: Chem. Rev. 1991, 91, 2, 119–135Publication Date (Print):March 1, 1991Publication History Published online1 May 2002Published … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTRegio- and stereochemical control in substitution reactions of cyclophosphazenesChristopher W. AllenCite this: Chem. Rev. 1991, 91, 2, 119–135Publication Date (Print):March 1, 1991Publication History Published online1 May 2002Published inissue 1 March 1991https://doi.org/10.1021/cr00002a002RIGHTS & PERMISSIONSArticle Views1028Altmetric-Citations308LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (3 MB) Get e-Alerts Get e-Alerts

Synthesis of β-Aminophosphonates and -Phosphinates

2005-02-11

Francisco Palácios , Concepción Alonso , Jesús M. de los Santos

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of β-Aminophosphonates and -PhosphinatesFrancisco Palacios, Concepción Alonso, and Jesús M. de los SantosView Author Information Departamento de Química Orgánica I, Facultad de Farmacia, Universidad del País … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of β-Aminophosphonates and -PhosphinatesFrancisco Palacios, Concepción Alonso, and Jesús M. de los SantosView Author Information Departamento de Química Orgánica I, Facultad de Farmacia, Universidad del País Vasco, Apartado 450, 01080 Vitoria, Spain Cite this: Chem. Rev. 2005, 105, 3, 899–932Publication Date (Web):February 11, 2005Publication History Received27 September 2004Published online11 February 2005Published inissue 1 March 2005https://pubs.acs.org/doi/10.1021/cr040672yhttps://doi.org/10.1021/cr040672yresearch-articleACS PublicationsCopyright © 2005 American Chemical SocietyRequest reuse permissionsArticle Views5326Altmetric-Citations317LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Ethyl groups,Hydrolysis,Organic compounds,Organophosphorus compounds,Reaction products Get e-Alerts

Synthesis and reaction chemistry of stable two-coordinate phosphorus cations (phosphenium ions)

1985-10-01

Alan H. Cowley , Richard A. Kemp

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis and reaction chemistry of stable two-coordinate phosphorus cations (phosphenium ions)A. H. Cowley and R. A. KempCite this: Chem. Rev. 1985, 85, 5, 367–382Publication Date (Print):October 1, … ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis and reaction chemistry of stable two-coordinate phosphorus cations (phosphenium ions)A. H. Cowley and R. A. KempCite this: Chem. Rev. 1985, 85, 5, 367–382Publication Date (Print):October 1, 1985Publication History Published online1 May 2002Published inissue 1 October 1985https://pubs.acs.org/doi/10.1021/cr00069a002https://doi.org/10.1021/cr00069a002research-articleACS PublicationsRequest reuse permissionsArticle Views2509Altmetric-Citations394LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Organophosphorus reagents in organic synthesis

1979-01-01

J. I. G. Cadogan

Synthesis of Carbon-Phosphorus Bonds

2003-12-18

Robert Engel

Synthesis of Carbon-Phosphorus Bonds, Second Edition is a working guide for the laboratory, incorporating classical approaches with the recent developments of carbon-phosphorus (C-P) bond formation. These advances include the preparation … Synthesis of Carbon-Phosphorus Bonds, Second Edition is a working guide for the laboratory, incorporating classical approaches with the recent developments of carbon-phosphorus (C-P) bond formation. These advances include the preparation of phosphoranes - specifically in the use of transient oxophosphoranes as intermediates in organophosphorus comp

Phosphorus-nitrogen Compounds

1972-01-01

31P and 13C NMR of Transition Metal Phosphine Complexes

1979-01-01

Paul S. Pregosin , Roland W. Kunz

Multiple bonds and low coordination in phosphorus chemistry

1990-01-01

Manfred Regitz , Otto J. Scherer , Rolf Appel

Handbook of Organophosphorus Chemistry

1992-06-19

Robert Engel

This practical work summarizes the development of organophosphorus chemistry in topical areas and details the discipline's current state - providing applications and experimental procedures throughout.;Written by 18 leading authorities in … This practical work summarizes the development of organophosphorus chemistry in topical areas and details the discipline's current state - providing applications and experimental procedures throughout.;Written by 18 leading authorities in the field, the Handbook of Organophosphorus Chemistry: examines advances in the mechanistic understanding of the Perkow and related organophosphorus reactions; describes methods for the reduction of quinquevalent to trivalent phosphorus and their applications to standard synthetic procedures; emphasizes the preparation of phosphonates bearing hydroxy, amino, and thiol functions at the alpha-position relative to the phosphoryl group; reviews the basics of NMR as it applies to the 31P nucleus, considering the use of the latest measurement techniques in solving structural and mechanistic problems; compares the characteristics of polymer-based and monomeric materials; and presents recent progress in the design of insecticides and covers their chemical and biological characteristics.;Generously referenced with close to 3000 bibliographic citations, the Handbook of Organophosphorus Chemistry is an important volume for organic, medicinal, and agricultural chemists and biochemists; pharmacists; chemical engineers; and graduate-level students in these disciplines.

Synthesis and Cytotoxic Activity of a New Family of α-Hydroxyphosphonates with the Benzothiophene Scaffold

2025-06-24

Mátyás Milen , Tamás Miklós John , Anna Sára Kis +6 more | Pharmaceuticals

Background: α-Hydroxyphosphonates, one of the most prominent classes of phosphonates, remain of utmost importance because of their potential and real biological activity as pharmaceutical or pesticide agents. The effect is … Background: α-Hydroxyphosphonates, one of the most prominent classes of phosphonates, remain of utmost importance because of their potential and real biological activity as pharmaceutical or pesticide agents. The effect is the consequence of their enzyme inhibitory properties. Objectives: It was planned to make available new heterocyclic hydroxyphosphonate derivatives with cytotoxic activity. Methods: After optimizing the synthesis, 23 members of a new family, α-hydroxy-α-(benzothiophen-2-yl)-methylphosphonates, were prepared by the Pudovik reaction of benzo[b]thiophene-2-carboxaldehydes and diethyl phosphite. The addition was performed at 26 °C in the presence of triethylamine as the catalyst. One of the products was also characterized by single-crystal X-ray analysis. Results: The cytotoxic effect of the α-hydroxy-α-benzothiophenyl-methylphosphonates was tested on U266 myeloma, A2058 melanoma, HT-29 colon, and EBC-1 lung cancer cell lines. Most of the molecules showed significant activity; the greatest effects were seen after treatment with hydroxyphosphonates with a trifluoromethyl group in the benzene ring. Conclusions: The cytotoxic activity of the newly synthesized α-hydroxyphosphonates is encouraging to find even better derivatives.

Fluorinated Aminophosphonates and Aminophosphonic Acids: A Journey Through Recent Advances

2025-06-23

Tomasz Cytlak , Monika Bilska‐Markowska , Marcin Kaźmierczak | European Journal of Organic Chemistry

This review aims to summarise the most recent developments in the chemistry of fluorinated aminophosphonates and aminophosphonic acids, with a particular focus on literature published since the turn of 2016/2017. … This review aims to summarise the most recent developments in the chemistry of fluorinated aminophosphonates and aminophosphonic acids, with a particular focus on literature published since the turn of 2016/2017. Fluorinated derivatives of aminophosphonates and aminophosphonic acids represent a rapidly growing area of interest due to their unique chemical properties and potential applications in various fields, including medicinal and agricultural chemistry. In this work, special emphasis is placed on highlighting the most significant reports concerning selective and efficient synthetic methodologies for these compounds. Particular attention is given to strategies that offer high yields, regio‐ or stereoselectivity, and operational simplicity, including direct fluorination, addition reactions, as well as catalytic and radical processes. Additionally, the review discusses the potential practical applications of these fluorinated derivatives, such as their roles as enzyme inhibitors, bioisosteres of amino acids, and potential pharmaceuticals.

5-Phosponohydantoins: synthesis and investigation of their biological activities

2025-06-23

Ivan A. Klimchuk , Dmitrii O. Shkil , Yury V. Timchenko +7 more | Research Square (Research Square)

<title>Abstract</title> Various 5-phosphono-hydantoins resembling SF2312 and bearing phosphonate moiety can be prepared from the starting hydantoins by a previously described two-step process via sequential bromination and phosphorylation to yield diethyl … <title>Abstract</title> Various 5-phosphono-hydantoins resembling SF2312 and bearing phosphonate moiety can be prepared from the starting hydantoins by a previously described two-step process via sequential bromination and phosphorylation to yield diethyl 5-phosphono-hydantoin esters followed by facile removal of ethyl groups. The insights of two-step bromination and phosphorylation were analyzed and described in respect of the known literature data. Given the structural similarity between hydantoin derivatives and glyphosate, we propose that hydantoins with a phosphonate group could serve as potential modulators of EPSP synthase mimicking glyphosate’s binding interactions and disrupting the shikimate pathway. During a test on hypersensitive <italic>E. coli</italic> strains, some hydantoins bearing phosphonate moiety showed a slight antibiotic activity and additionally were shown to have phytotoxicity causing local chlorotic lesions on punctured leaf segments of three plant species. Molecular modelling was applied to understand the biological activity of synthesized hydantoins.

Synthesis of β-ketophosphonates through aerobic copper(II)-mediated phosphorylation of enol acetates

2025-06-20

Alexander S. Budnikov , Igor B. Krylov , Fedor K. Monin +5 more | Beilstein Journal of Organic Chemistry

Aerobic copper(II)-mediated phosphorylation of enol acetates with H-phosphonates leading to the formation of β-ketophosphonates was discovered. The proposed method is applicable to a wide range of H-phosphonates or phosphine oxides … Aerobic copper(II)-mediated phosphorylation of enol acetates with H-phosphonates leading to the formation of β-ketophosphonates was discovered. The proposed method is applicable to a wide range of H-phosphonates or phosphine oxides as PH-reagents and enol acetates. Unlike previous reports, which generally employed stoichiometric amounts of oxidants or more expensive transition metal catalysts, the present protocol employs only cheap copper sulfate pentahydrate as a catalyst under mild reaction conditions. The achieved phosphorylation proceeds via the formation of P-centered radicals produced by the oxidation of PH-reagents by copper(II)-containing species. Employing anhydrous CuSO 4 instead of the pentahydrate led to a dramatic phosphorylation yield drop from 70 to <5%. It seems that the ligand environment of copper is very important for the effective reaction: other Cu(II) and Cu(I) salts, including halides, nitrate, tetrafluoroborate, or perchlorate, were much less effective or completely inert.

Modular Access to P(V)‐Stereogenic Compounds via Cu‐Catalyzed Desymmetrization of (Thio)Phosphonic Dichlorides

2025-06-17

Hong-Qing Yao , Yueming Cai , Tian Xie +4 more | Angewandte Chemie

Chiral phosphorus(V) centers—particularly those bearing fully heteroatom‐substituted frameworks—are key stereochemical motifs in pharmaceuticals, nucleic acid therapeutics, and functional materials. However, their stereoselective construction remains a long‐standing challenge in synthetic chemistry. … Chiral phosphorus(V) centers—particularly those bearing fully heteroatom‐substituted frameworks—are key stereochemical motifs in pharmaceuticals, nucleic acid therapeutics, and functional materials. However, their stereoselective construction remains a long‐standing challenge in synthetic chemistry. Here we report a copper‐catalyzed desymmetrization strategy enabled by rationally engineered PIM ligands that affords broad and modular access to structurally diverse P(V)‐stereogenic compounds. By harnessing the tunable Lewis acidity and well‐defined chiral environment of the catalyst—together with the distinct mechanistic features of chiral Lewis acid catalysis—this strategy overcomes the substrate scope limitations that have constrained traditional approaches. The method demonstrates broad functional group tolerance and delivers high levels of stereocontrol across seven distinct substitution patterns, including the efficient construction of chiral P=S motifs previously considered synthetically challenging. Importantly, the approach enables efficient late‐stage derivatization of nucleosides and their analogs, thereby providing a general entry point to stereodefined P(V)‐containing bioactive molecules. This work not only expands the utility of transition‐metal Lewis acid catalysis in phosphorus chemistry, but also establishes a versatile framework for applications in drug discovery and nucleic acid‐based therapeutics where precise stereochemical control is essential.

(η4-Trimethylenemethane)(1,1,1-tris{[bis(4-methoxyphenyl)phosphanyl]methyl}ethane)ruthenium(II) diethyl ether hemisolvate

2025-06-17

Carolin A. M. Stein , Elisabetta Alberico , Anke Spannenberg +2 more | IUCrData

The title compound, [Ru(C 47 H 51 O 6 P 3 )(C 4 H 6 )]·0.5C 4 H 10 O, consists of an Ru II atom coordinated by 1,1,1-tris{[bis(4-methoxyphenyl)phosphanyl]methyl}ethane in … The title compound, [Ru(C 47 H 51 O 6 P 3 )(C 4 H 6 )]·0.5C 4 H 10 O, consists of an Ru II atom coordinated by 1,1,1-tris{[bis(4-methoxyphenyl)phosphanyl]methyl}ethane in κ 3 -coordination mode and an η 4 -coordinating trimethylenemethane ligand. The complex molecule is co-crystallized with a diethyl ether solvent molecule. A half diethyl ether molecule was considered, whereas additional disordered solvent molecules were removed from the diffraction data with the SQUEEZE procedure in PLATON [Spek (2015). Acta Cryst . C 71 , 9–18].

FIVE-MEMBERED ZIRCONACARBOCYCLES IN THE SYNTHESIS OF PHOSPHOLANES AND PHOSPHOLS

2025-06-16

A. L. Makhamatkhanova , Denis Sh. Sabirov | Izvestia Ufimskogo Nauchnogo Tsentra RAN

The review summarizes and systematizes data on methods for the synthesis of substituted phospholanes and phospholes based on the reaction of five-membered zirconacarbocycles obtained in situ by catalytic cyclometallation of … The review summarizes and systematizes data on methods for the synthesis of substituted phospholanes and phospholes based on the reaction of five-membered zirconacarbocycles obtained in situ by catalytic cyclometallation of unsaturated compounds (alkenes, alkynes or dienes) into phosphacarbocycles using alkyl (aryl) phosphorus dihalides. The high reactivity of zirconacarbocycles allows one to obtain cyclic organophosphorus compounds (OPCs) under mild conditions, with high yields and in virtually one preparative step, which makes this approach extremely popular.

Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and Their Derivatives

2025-06-13

C. T. Bedford | Organic Reaction Mechanisms/Organic reaction mechanisms

Organophosphorus Chemistry

2025-06-05

This annual review of the literature provides a comprehensive and critical survey of a vast field of study involving organophosphorus compounds, ranging from phosphines, phosphine-related P–C bonded compounds and their … This annual review of the literature provides a comprehensive and critical survey of a vast field of study involving organophosphorus compounds, ranging from phosphines, phosphine-related P–C bonded compounds and their chalcogenide derivatives, phosphonium salts and P-ylides, to tervalent and quinquevalent phosphorus acid derivatives and penta- and hexa-coordinated phosphorus compounds. Recent developments in applications as reagents in green synthetic procedures are also given. With an emphasis on interdisciplinary content, this book will appeal to the worldwide organic chemistry and engineering research communities.

Bioactive Dioxo-Phosphobetaines derived from the reaction of Dichlorodinitrobenzofuroxane with various phosphines

2025-06-01

И. В. Галкина , Haiyan Fan , S. R. Romanov +5 more | Bioorganic Chemistry

Synthesis of 2-Phosphorus-Substituted Indoles via Ring Expansion of Benzocyclobutenone Oxime Sulfonates

2025-05-29

Yusuke Kanno , Yumi Yamashita , Akira Sugiyama +3 more | Organic Letters

A method for the synthesis of 2-phosphorus-substituted indoles via ring expansion of benzocyclobutenone oxime sulfonates, which were prepared via the [2 + 2] cycloaddition of benzynes and ketene acetals, and … A method for the synthesis of 2-phosphorus-substituted indoles via ring expansion of benzocyclobutenone oxime sulfonates, which were prepared via the [2 + 2] cycloaddition of benzynes and ketene acetals, and subsequent oximization and sulfonylation was developed. The reaction occurs by addition of the phosphate anion or phosphine oxide anion to the C═N bond of oxime sulfonates, followed by ring expansion to provide 2-phosphorus-substituted indoles. This method was applicable to the synthesis of 2-phosphorus-substituted indoles with a wide variety of substitution patterns on the benzene ring and at the 3-position, as well as to a 2-phosphorus-substituted 4-aza-indole. An indol-2-ylphosphonic acid and a 2-phosphaneylindole were obtained by a transformation of the corresponding products. This protocol was applied to synthesize a duocarmycin SA phosphonate analogue, which exhibited greater cytotoxicity against HeLa S3 and KPL-4 cells than duocarmycin SA.

Lewis Acid-Mediated Deoxygenative Synthesis of Trivalent Sterically Hindered Phosphines from Aldehydes

2025-05-29

Xiaoqiang Wu , Abuduwaili Alimu , Wei Zhong +1 more | Organic Letters

The efficient synthesis of trisubstituted trivalent phosphines remains challenging. Herein, we report a novel approach for rapid construction of these compounds from aldehydes under Lewis acid-mediated conditions. By using sterically … The efficient synthesis of trisubstituted trivalent phosphines remains challenging. Herein, we report a novel approach for rapid construction of these compounds from aldehydes under Lewis acid-mediated conditions. By using sterically hindered disubstituted phosphines, aldehydes can undergo a deoxygenative reaction to afford trivalent phosphorus compounds. This modular and practical method is characterized by operational simplicity, a broad substrate scope, and excellent functional group tolerance, which holds great potential for applications in organic synthesis.

Tandem Phosphorodithiolation/Rearrangement of Allylic Alcohols with P4S10 and Alcohols to Construct Allylic Phosphorodithioates

2025-05-29

Jian Huang , Yingjie Wang , Yufen Lv +4 more | The Journal of Organic Chemistry

An additive-free approach has been developed for the synthesis of allylic phosphorodithioates through tandem phosphorodithiolation/rearrangement of allylic alcohols with P4S10 and alcohols. The reaction proceeds under mild conditions and provides … An additive-free approach has been developed for the synthesis of allylic phosphorodithioates through tandem phosphorodithiolation/rearrangement of allylic alcohols with P4S10 and alcohols. The reaction proceeds under mild conditions and provides a practical protocol to prepare a series of allylic phosphorodithioates in moderate to good yields.

Mechanistic Insights into Enhanced Reactivation of Organophosphate-Inhibited Enzymes by Methyl-Substituted 2-Pralidoxime Analogs

2025-05-27

Phiphob Naweephattana , Nalinee Kongkaew , Panida Surawatanawong +7 more

Organophosphate (OP) compounds, such as paraoxon (POX), inhibit enzymes critical for neurotransmission, causing severe neurotoxic effects. Pralidoxime (2-pyridine aldoxime methyl chloride) or 2-PAM is commonly employed to reverse this inhibition, … Organophosphate (OP) compounds, such as paraoxon (POX), inhibit enzymes critical for neurotransmission, causing severe neurotoxic effects. Pralidoxime (2-pyridine aldoxime methyl chloride) or 2-PAM is commonly employed to reverse this inhibition, but its reactivation efficiency is limited. This study computationally explores the reactivation mechanisms of 2-PAM and its methyl-substituted analogs, 4-methyl-2-PAM (4-Met-2-PAM), and 4,6-dimethyl-2-PAM (4,6-Dimet-2-PAM). The reactivation process involves several key steps, such as hydrogen transfer and nucleophilic substitution (SN2). Introducing methyl groups at positions 4 and 6 increases the negative charge on the oxime oxygen, improving nucleophilicity and reactivity. Both 4-Met-2-PAM and 4,6-Dimet-2-PAM show better reactivity than 2-PAM, with 4,6-Dimet-2-PAM demonstrating the greatest improvement. This enhanced reactivity shifts the rate-determining step from nucleophilic substitution to the initial hydrogen transfer. These findings offer valuable insights for designing more effective oxime-based antidotes for organophosphate poisoning.

Eco-friendly TiO2–ZnO nano-catalysts: synthesis, catalytic performance in synthesis of α-amino/hydroxyphosphonates and their ADME, docking and antimicrobial studies

2025-05-27

Ravindra Reddy Ummadi , Venkata Nadh Ratnakaram , Subba Rao Devineni +2 more

A Straightforward Approach Towards Phosphadecalones by Microwave-Assisted Diels–Alder Reaction

2025-05-27

Elżbieta Łastawiecka , A.E. Kozioł , K. Michał Pietrusiewicz

A stereoselective and scalable strategy for the synthesis of phosphorus-containing bicyclic and tricyclic compounds from 1-phenylphosphin-2-en-4-one 1-oxide is presented. This activated dienophile, available in both racemic and enantiopure forms, undergoes … A stereoselective and scalable strategy for the synthesis of phosphorus-containing bicyclic and tricyclic compounds from 1-phenylphosphin-2-en-4-one 1-oxide is presented. This activated dienophile, available in both racemic and enantiopure forms, undergoes smooth [4+2] cycloadditions with acyclic and cyclic dienes, affording products with excellent yields and controlled stereochemistry. Notably, the cis/trans-fusion of the cycloadducts (phosphadecalones and phosphahexahydrochrysene) can be selectively controlled by fine-tuning the conditions of microwave-assisted cycloaddition reaction. The influence of temperature, time, and steric effects on cis/trans and endo/exo selectivity was examined in detail. The molecular structure, including the absolute configuration, of eight products has been determined by X-ray crystallography. These analyses further established the endo-selective nature of the cycloaddition, favoring the P=O face of the dienophile. Post-cycloaddition transformations of selected P-stereogenic phosphadecalone, such as isomerization, reduction and deoxygenation, demonstrate the synthetic versatility of the resulting products.

Diisopropyl (E)-(1-hydroxy-3-phenylallyl)phosphonate

2025-05-27

Alun R. Coker , Aidan P. McKay , David B. Cordes +1 more | Molbank

We report the synthesis and the molecular structure as determined by single-crystal X-ray diffraction of diisopropyl (E)-(1-hydroxy-3-phenylallyl)phosphonate. The compound was fully characterised by 1H, 13C, and 31P NMR spectroscopy, IR … We report the synthesis and the molecular structure as determined by single-crystal X-ray diffraction of diisopropyl (E)-(1-hydroxy-3-phenylallyl)phosphonate. The compound was fully characterised by 1H, 13C, and 31P NMR spectroscopy, IR spectroscopy, and Mass Spectrometry.

Innovative Cyclic Nucleotides ‐ Nucleoside 2’,3’‐Seven Membered Cyclic Diphosphonate Derivatives. Theoretical Feasibility, Synthesis, and Properties

2025-05-26

Bilha Fischer , S. S. Liberman , Lea Bobot +2 more

7-membered cyclic nucleotides have remained unknown despite the natural abundance of their 5- and 6-membered counterparts. Here, we report the first synthesis of 2',3'-cyclic nucleosides (tetrathio)diphosphonate (2',3'-cNTDPs) by a rapid … 7-membered cyclic nucleotides have remained unknown despite the natural abundance of their 5- and 6-membered counterparts. Here, we report the first synthesis of 2',3'-cyclic nucleosides (tetrathio)diphosphonate (2',3'-cNTDPs) by a rapid one-step, regioselective, and protection-free reaction of U, A, C, I, and G, with methylene-bis(1,3,2-dithia-phospholane-2-sulfide) (DTPS). The reaction proceeds instantaneously, even at -35 °C, resulting in the quantitative conversion of methylene-bis-DTPS. Density functional theory (DFT) calculations of ∆Gr confirm the synthetic feasibility and regioselectivity, attributing the efficiency to strain release in DTPS rings and entropic gain from thiirane elimination. The resulting 2',3'-cNTDPs exhibited remarkable hydrolytic stability and greater solution structural rigidity than free nucleosides.

Chemical Synthesis of Glycosyl Boranophosphates Using Phosphonic Acid Derivatives

2025-05-24

Kazuki Sato

Chemical Synthesis of Glycosyl Boranophosphates Using Phosphonic Acid Derivatives

2025-05-24

Kazuki Sato

Unraveling the influence mechanisms of different substituents on the chemical activity of N-heterocyclic phosphines via theoretical calculations

2025-05-21

Yilei Chen

First Synthesis of All of the cis-Fused Stereoisomers of Phosphonic and Phosphinic Analogues of Octahydrocyclopenta[b]pyrrole-2-carboxylic Acid

2025-05-20

Mario Ordóñez , José Luis Viveros‐Ceballos , Héctor Gustavo Ruiz-Ponce

Abstract We present the first stereoselective synthesis of phosphonic and phosphinic analogues not only of (2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylic acid, the pivotal intermediate in ramipril synthesis, but also of all its cis-fused stereoisomers. … Abstract We present the first stereoselective synthesis of phosphonic and phosphinic analogues not only of (2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylic acid, the pivotal intermediate in ramipril synthesis, but also of all its cis-fused stereoisomers. Key to this accomplishment is the highly diastereoselective synthesis of cis-fused bicyclic (3aS,6aS)- and (3aR,6aR)-hexahydrocyclopenta[b]pyrrol-2-one using Meyers’ tricyclic lactam methodology. The nucleophilic addition of trimethyl phosphite or dimethyl phenylphosphonite to chiral N-acyliminium ions affords the diastereoisomers, which are easily separated by column chromatography. The diastereoselectivity in the nucleophilic addition of the phosphorus reagents is completely consistent with our previous reports and all synthesized compounds were fully characterized.

Retraction of “Photoelectrochemical Synthesis of Benzo[b]phosphole Oxides via Sequential P–H/C–H Bond Functionalizations”

2025-05-19

Nayan Saha , Burkhard Koenig

Synthesis of Diversely Substituted Diethyl (Pyrrolidin-2-Yl)Phosphonates

2025-05-07

Andrea Bagán , Alba López-Ruiz , Sònia Abás +5 more

Imidazoline I2 receptors (I2-IR) are untapped therapeutic targets lacking a structural description. Although the levels of I2-IR are dysregulated in a plethora of illnesses, the arsenal of ligands that can … Imidazoline I2 receptors (I2-IR) are untapped therapeutic targets lacking a structural description. Although the levels of I2-IR are dysregulated in a plethora of illnesses, the arsenal of ligands that can modulate I2-IR is limited. In this framework, we have reported several new structural families embodying the iminophosphonate functional group that have an excellent affinity and selectivity for I2-IR, and selected members have demonstrated relevant pharmacological properties in murine models of neurodegeneration and Alzheimer’s disease. Starting with these iminophosphonates, we continued to exploit their high degree of functionalization through a short and efficient synthesis to access unprecedented 2,3-di, 2,2,3-tri, 2,3,4-tri, and 2,2,3,4-tetrasubstituted diethyl (pyrrolidine-2-yl) phosphonates. The stereochemistry of the new compounds was unequivocally characterized by X-ray crystallographic analyses. Two selected compounds with structural features shared with the starting products were pharmacologically evaluated, allowing us to deduce the required key structural motifs for biologically active aminophosphonate derivatives.

Stereoselective Synthesis of Nucleotide Analog Prodrugs (ProTides) via an Oxazaphospholidine Method

2025-05-07

M. Nakamura , Kiyoshi Kakuta , Kazuki Sato +1 more

This paper describes the stereocontrolled synthesis of O-aryl phosphoramidate nucleotide prodrugs (ProTides), namely Remdesivir, Sofosbuvir, and NUC-1031, using an oxazaphospholidine method. The 5'-phosphoramidate derivatives were synthesized via a one-pot process … This paper describes the stereocontrolled synthesis of O-aryl phosphoramidate nucleotide prodrugs (ProTides), namely Remdesivir, Sofosbuvir, and NUC-1031, using an oxazaphospholidine method. The 5'-phosphoramidate derivatives were synthesized via a one-pot process involving the condensation of nucleoside 5'-oxazaphospholidine derivatives with phenol, bromination of the resulting phosphite using N-bromosuccinimide, and subsequent reaction with an amine. The target compounds were obtained with high stereoselectivity (dr >99:1). This one-pot strategy substantially reduced the reaction time from those of traditional phosphorylation methods using P(V) derivatives, providing an efficient and streamlined route to ProTides.

Efficient, neat method for the synthesis of pyrazolyl phosphonates by di- n -butylamine

2025-05-06

M Indhupriya , Reddi Mohan Naidu Kalla , Sowjanya Bandlapalli +2 more

Synthesis and Characterisation of Tris(2,4-xylyl)phosphane oxide and the Heavier Chalcogen Derivatives of Tris(2,4-xylyl)- and Tris(3,5-xylyl)phosphane

2025-05-02

Kathleen L. May , Matthew C. Hill , Alan J. Lough +1 more

The synthesis and characterisation of the novel sulfide and selenide adducts of both tris(2,4-xylyl)phosphane (i.e., 1; S adduct: 3; Se material: 4) and tris(3,5-xylyl)phosphane (5) are reported (S: 7; Se: … The synthesis and characterisation of the novel sulfide and selenide adducts of both tris(2,4-xylyl)phosphane (i.e., 1; S adduct: 3; Se material: 4) and tris(3,5-xylyl)phosphane (5) are reported (S: 7; Se: 8) in addition to the previously unknown oxide of 1 (viz., 2). The heavier Group 16 (Selenium) compounds 4 and 8 were produced by a rarely used photochemical protocol employing dialkyldiselenides as the Se source. Attempts to obtain the elusive selenide complex of trimesitylphosphane (9: i.e., tris(2,4,6-trimethylphenyl)phosphane) by this and other previously untried methods is also detailed but were ultimately unsuccessful. These observations further support the surmised instability and / or inaccessible nature of the selenide adduct of 9. Crystals of both 3 and 4 were obtained in the monoclinic P21/c space group each with two unique molecules in the unit cell; the 3,5-congeners 7 and 8 are found in the trigonal R3c space group. Compound 2 was found to crystallize in space group C2/c. The isolated and examined crystalline material obtained from bulk 8 is found to contain 81.0% of the phosphane-selenide with the residual lattice sites being occupied by selenide-free 5. The solid-state structural aspects of the examples reported herein are discussed and are placed into context with other (aryl)3P=E (E = O, S or Se) materials.

SYNTHESIS OF PHOSPHORYLATED ACETAMIDINES AND THEIR CONDENSATION WITH ACETALDEHYDE

2025-05-01

Е. В. Шишкин , Олена Валеріївна Аніщенко , М. А. Шевченко +2 more

Synthesis of phosphorylated acetamidines unsubstituted by the imino group was carried out, and their interaction with acetaldehyde was studied. Amidines having a hydrogen atom in the imino group have been … Synthesis of phosphorylated acetamidines unsubstituted by the imino group was carried out, and their interaction with acetaldehyde was studied. Amidines having a hydrogen atom in the imino group have been found to react with acetaldehyde under mild conditions to form relatively stable carbonyl group adducts. In synthesized compounds, various types of biological activity are predicted that may be useful for agriculture and medicine.

In Vitro Antimicrobial Activity and In Silico Study of Phosphonamide Derivatives: Interaction with Dihydropteroate Synthase

2025-05-01

Djenet Amel Dehmchi , Fouzia Bouchareb , Malika Berredjem +4 more

Abstract This work presents a comprehensive evaluation of a series of previously synthesized phosphonamide compounds, focusing on their biological potential and physicochemical properties. The synthesized phosphonamides were subjected to in … Abstract This work presents a comprehensive evaluation of a series of previously synthesized phosphonamide compounds, focusing on their biological potential and physicochemical properties. The synthesized phosphonamides were subjected to in vitro biological activity testing. To further validate the observed bioactivities, we conducted in silico investigations, including density functional theory (DFT) calculations, ADMET (absorption, distribution, metabolism, excretion, and toxicity) predictions, and molecular docking analyses. The in vitro antimicrobial assays demonstrated promising therapeutic potential for the phosphonamide derivatives. The in silico studies provided valuable insights into the physicochemical properties, drug‐likeness, and probable binding interactions of the synthesized compounds with dihydropteroate synthase. DFT calculations, ADMET predictions, and molecular docking analyses collectively suggest the favorable profiles of the phosphonamides, highlighting their potential as viable drug candidates for further development.

Abstract 2725 The Chemistry of Community

2025-05-01

Mechthild Pohlschröder , T. R. Gopalakrishnan Nair , Jean-Marie Kouassi | Journal of Biological Chemistry

Epimerization mechanism of P-spiro chiral tetraaminophosphoniums: effect of nitrogen substituents and counter ions

2025-05-01

Yaoki Kansaku , Yoshitaka Aramaki , Daisuke Uraguchi +1 more

Abstract The key factors determining the feasibility of epimerization of P-spiro chiral tetraaminophosphoniums have been elucidated by DFT calculations. P-Spirochirality inversion proceeds through the formation of a pentacoordinate phosphorane by … Abstract The key factors determining the feasibility of epimerization of P-spiro chiral tetraaminophosphoniums have been elucidated by DFT calculations. P-Spirochirality inversion proceeds through the formation of a pentacoordinate phosphorane by the nucleophilic attack of the counter ion and the subsequent pseudorotation via the square pyramidal transition state (TS). The TS energies are highly dependent on the nitrogen substituents of the aminophosphoniums and the counter ion structure. The energy barrier for the TS significantly increases by the introduction of methyl groups on two of the four nitrogen atoms of the aminophosphonium because of their steric repulsion. On the other hand, the energy barrier decreases when oxyanions, such as nitronate and phenoxide, are involved due to the effective interaction of the oxyanion p-orbitals with P–N σ* orbitals unlike the case with chloride ions. These profiles will account for our experimental observations.

Nano-ZnO catalyzed microwave synthesis of novel α-aminophosphonates: anti-diabetic potential via molecular docking, ADMET analysis, and α-amylase and α-glucosidase inhibition studies

2025-04-29

Vishal Govind Rao , A. Hanumatha Rao , Ch. Subramanyam +3 more

Bridging Homogeneous and Heterogeneous Catalysis: Ni@CPOL-dppp&PPh3-Catalyzed Symmetric H-Phosphonate Diester Synthesis from Sodium Hypophosphite

2025-04-29

Jin Yang , Dang‐Wei Qian , Hongli Wang +2 more

Recent Advances in Phosphonium Salts‐Mediated Synthetic Transformations

2025-04-24

Abhishek Kumar , Mohammad Roshan Shoaib Savanura , Saksham Garg +3 more

Phosphonium salts have gained significant importance in the rapid construction of biologically active natural and synthetic heterocyclic and carbocyclic scaffolds. This review summarizes recent advances in the catalytic applications and … Phosphonium salts have gained significant importance in the rapid construction of biologically active natural and synthetic heterocyclic and carbocyclic scaffolds. This review summarizes recent advances in the catalytic applications and reagent‐based studies of phosphonium salts from 2010 to 2024. Each scheme highlights the characteristic substrates, corresponding final products, and the required reaction conditions. Additionally, key phosphonium‐catalyzed reactions, including alkylation, allylation, arylation, Wittig reaction, annulation, indole synthesis, thiophene and furan synthesis, and carbonyl compound preparation, are discussed in terms of their scope, classification, and plausible mechanisms. Over the past decade, phosphonium salts have consistently demonstrated their versatility in chemical transformations through modifications in catalytic systems.

Highly effective, rapid and convenient one-pot synthesis of O,O’ -dialkyl- N,N -dialkylphosphoramidates from trialkyl phosphites

2025-04-23

Sweeti , Pauline Malik , Gyanesh Mishra +4 more

Trivalent Phospha-Brook rearrangement enabled practical deoxygenative phosphonylation of carbonyls

2025-04-16

Xiaoqiang Wu , Shanya Lu , Wei Zhong +1 more

Brønsted base-mediated [1,2]-phospha-Brook rearrangements have garnered considerable attention for developing new methodologies and efficiently constructing complex molecular structures. However, the strict reliance on pentavalent phosphonates imposes strong limitations on the … Brønsted base-mediated [1,2]-phospha-Brook rearrangements have garnered considerable attention for developing new methodologies and efficiently constructing complex molecular structures. However, the strict reliance on pentavalent phosphonates imposes strong limitations on the reaction types, and the mechanistic constraint also excludes the involvement of trivalent phosphine in the same pathway. In this study, we employ Lewis acid rather than Brønsted base to shift the charge transfer from the previous O-P-C direction to a P-C-O process. This orthogonal approach can undergo the unprecedented C-O bond cleavage instead of traditional C-P bond splitting and enables the deoxygenative phosphorylation of carbonyl compounds under metal-free conditions to rapid access various tertiary phosphine oxides. The reaction demonstrates excellent substrate scope, remarkable functional group compatibility, and operational simplicity, offering significantly enhanced atom-economy compared to previous deoxygenative strategies. Additionally, detailed mechanistic studies reveal an unusual oxygen atom crossover and clearly elucidate the mechanism of this Lewis acid-mediated trivalent phospha-Brook rearrangement. These insights further deepen the understanding of trivalent phosphorus chemistry and pave the way for the design of related reactions.