72696-92-5Relevant articles and documents
Synthesis of 2-(arylamino)ethyl phosphonic acids via the aza-Michael addition on diethyl vinylphosphonate
Bou Orm, Nadine,Dkhissi, Yasmina,Daniele, Stéphane,Djakovitch, Laurent
, p. 115 - 121 (2013/01/15)
A simple way of synthesising 2-(arylamino)ethyl phosphonic esters and acids via the aza-Michael addition of amines to diethyl vinylphoshonate 'on water' was developed. Various 2-(arylamino)ethyl phosphonates were initially produced through the condensation of primary and secondary amines with diethyl vinylphosphonate, focussing on those bearing one aromatic moiety, giving generally good to high yields (i.e.; 75-100%). These phosphonic esters were then hydrolysed in presence of bromomethylsilane to give quantitatively the corresponding phosphonic acids.
Aminobenzylation d'aldehydes phosphoniques: preparation d'acides aminoalkylphosphoniques
Fabre, Genevieve,Collignon, Noel,Savignac, Philippe
, p. 2864 - 2869 (2007/10/02)
The reaction of phosphonic aldehydes with benzylamine in presence of NaBH3CN yields benzylaminoalkylphosphonates which, submitted to catalytic hydrogenation, lead to phosphonic amino esters.When reductive amination is carried out with H2/Pd reduction and debenzylation are observed simultaneously.In the absence of reducing agent the enaminobenzylphosphonate can be isolated and N-alkylated.Hydrolysis of phosphonic amino-esters with dilute HCl gives phosphonic amino acids.The order of occurence of each operation, as well as the choice of the catalyst is discussed.