Aminophosphonic Acids - Phosphorus Analogues of Natural Amino Acids.Part 1: Syntheses of α-Aminophosphonic Acids

Zbigniew      H. Kudzin; Marcin      H. Kudzin; Jozef      Drabowicz; Chris      V. Stevens

doi:10.2174/138527211795703612

Abstract

This review presents a comprehensive account of methods which are commonly applied for the synthesis of α- aminophosphonic acids. In the following order, protocols based on the methodologies listed below are discussed: a) simultaneous formation of P-CN systems; b) nucleophilic substitution with phosphoroorganic nucleophiles; c) additions of the P-H functions to multiple C-N bonds; d) α – amination of phosphonates and functionalized alkylphosphonates; e) modifications of the side chain of aminoalkylphosphonates; f) modifications of phosphorus functions and h) modifications of functions containing nitrogen.

Keywords: α-aminophosphonic acids, α-aminophosphonates, phosphorus analogues of natural amino acids, methods of synthesis of α-aminophosphonic acids, Arbusov reaction, Kabachnik-Medved reaction, Fields reaction, Michaelis-Becker reaction, Moedritzer-Irani reaction, Birum reaction, Birum-Oleksyszyn reaction, Oleksyszyn reaction, PTC-aminoalkylphosphonate method, hydrophosphonylation of multiple C-N bonds compounds, 1-amination of functionalized phosphonates, C-alkylation of phosphonoglycine derivatives, Wittig-Horner reaction, abbreviation code system for α-aminophosphonates, phosphoroorganic nucleophiles, phosphoroorganic electrophiles, urylenebisalkanephosphonates (UBAP), Kabachnik-Fields Reaction, Mannich-type condensation procedure, Birum type Condensations, Arbuzov and Michaelis-Becker reactions, chiral thiourea, hydrazones, nitrones, POTMS fragments