Synthesis of 2-(arylamino)ethyl phosphonic acids via the aza-Michael addition on diethyl vinylphosphonate

被引：13
|
作者：
Orm, Nadine Bou [1 ]
Dkhissi, Yasmina [1 ]
Daniele, Stephane [1 ]
Djakovitch, Laurent [1 ]
机构：
[1] Univ Lyon, CNRS, Inst Rech Catalyse & Environm Lyon, IRCELYON,UMR 5256, F-69626 Villeurbanne, France
来源：
TETRAHEDRON | 2013年 / 69卷 / 01期
关键词：
beta-Aminophosphonic esters; beta-Aminophosphonic acids; 'On water' aza-Michael addition; Selective phosphonic ester hydrolysis; BETA-AMINOPHOSPHONATES; AMINES; VINYL;
D O I：
10.1016/j.tet.2012.10.059
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：115 / 121
页数：7
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