Acylphosphonamidates and ?-hydroxyiminophosphonamidates. Synthesis of N-acylphosphordiamidates by Beckmann rearrangement. Crystal structure of (E)-?-hydroxyiminobenzyl-1-pyrrolidinylphosphinate

Breuer, Eli; Zaher, Hisham; Tashma, Zeev; Gibson, Dan

doi:10.1002/(sici)1098-1071(199611)7:6<515::aid-hc13>3.0.co;2-t

Cited by 13 publications

(1 citation statement)

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“…For instance, Breuer et al described the synthesis of a series of acyl phosphonamidates using methyl benzoylphosphonochloridate and a series of amines in DCM in the presence of pyridine or excess amine. 20 Unfortunately, the products could not be isolated in pure form. Facing similar challenges and despite their prevalence as synthetic precursors to oligonucleotides, phosphoramidites have been rarely used as nucleophilic starting materials to access phosphonamidates.…”

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Solventless synthesis of acyl phosphonamidates, precursors to masked bisphosphonates

Crossey

Migaud

2015

Chem. Commun.

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A series of acyl phosphonamidates, the synthetic precursors to bisphosphonates, have been readily prepared from phosphoramidite type reagents and a range of acid chlorides. These reactions were performed using solventless conditions, where purification was easily achieved using column chromatography with yields ranging from 71-90%. Furthermore, we have demonstrated that these acyl phosphonamidates could be used for the preparation of unsymmetrical bisphosphonates, which do date are scarcely reported in the literature.

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Solventless synthesis of acyl phosphonamidates, precursors to masked bisphosphonates

Crossey

Migaud

2015

Chem. Commun.

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Phosphorus Derivatives of Hydroxylamines, Oximes and Hydroxamic Acids

Palácios

Santos

Vicario

et al. 2010

Patai's Chemistry of Functional Groups

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This comprehensive chapter, organized in three different sections, includes new topics focused on preparation and synthetic applications of phosphorus functionalized hydroxylamines, oximes and hydroxamic acids. The first section comprises the synthesis of phosphorus O ‐substituted hydroxylamines either through phosphorus‐oxygen or nitrogen‐oxygen single bond formation. The synthesis of N ‐substituted hydroxylamines is also covered in this first section by means of phosphorus‐nitrogen or carbon‐nitrogen bond formation reactions. This section also includes several transformations of phosphorus substituted hydroxylamines including among others: rearrangement, hydrolysis, reduction and oxidation reactions. Functionalized oximes containing phosphorus substituents including O ‐ and C ‐substituted oximes, and oximes with α‐ and β‐phosphorated moieties are covered in a second section. This provides an introduction to the common approaches to synthesize phosphorus substituted oximes, and the application of phosphorated oximes to the preparation of more elaborated compounds have been described. Some of the synthetic applications methods covered in the second section are fragmentation and rearrangement reactions, nucleophilic substitution at the phosphorus atom, intramolecular reactions, radical reactions, reduction of carbon‐nitrogen double bond, oxidation reactions, olefination reactions, dehydratation of oximes. The third section is dedicated to the synthesis and reactivity of phosphorus O ‐, N ‐, and C ‐substituted hydroxamic acid derivatives, spanning the few reports in the literature covering this topic. An extensive and current list of references and a subject index complete the chapter. Phosphorus Substituted Hydroxylamine Derivatives Phosphorus Substituted Oximes Phosphorus Substituted Hydroxamic Acid Derivatives Acknowledgments

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ChemInform Abstract: Acylphosphonamidates and α‐Hydroxyiminophosphonamidates. Synthesis of N‐Acylphosphordiamidates by Beckmann Rearrangement. Crystal Structure of (E)‐α‐Hydroxyiminobenzyl‐1‐ pyrrolidinylphosphinate.

et al. 1997

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Acylphosphonamidates and ?-hydroxyiminophosphonamidates. Synthesis of N-acylphosphordiamidates by Beckmann rearrangement. Crystal structure of (E)-?-hydroxyiminobenzyl-1-pyrrolidinylphosphinate

Cited by 13 publications

References 22 publications

Solventless synthesis of acyl phosphonamidates, precursors to masked bisphosphonates

Solventless synthesis of acyl phosphonamidates, precursors to masked bisphosphonates

Phosphorus Derivatives of Hydroxylamines, Oximes and Hydroxamic Acids

ChemInform Abstract: Acylphosphonamidates and α‐Hydroxyiminophosphonamidates. Synthesis of N‐Acylphosphordiamidates by Beckmann Rearrangement. Crystal Structure of (E)‐α‐Hydroxyiminobenzyl‐1‐ pyrrolidinylphosphinate.

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