Tetrahedron letters

First synthesis of 2-[alkylamino (diethoxyphosphoryl) methyl] acrylic ethyl esters

H Kraı̈em, MI Abdullah, H Amri

Index: Kraiem, Houda; Abdullah, Meysun Ibrahim; Amri, Hassen Tetrahedron Letters, 2003 , vol. 44, # 3 p. 553 - 555

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Citation Number: 13

Abstract

The ethyl α-bromomethyl-β-(diethoxyphosphoryl) acrylic acid ester 9 has been prepared by addition of bromine to allylphosphonate 7 then dehydrobromination with DBU in acetonitrile. Reaction of allylic bromide 9 with primary amines in a bimolecular SN2′-type mecanism in methanol at low temperature, gives rise to the 2-[alkylamino (diethoxyphosphoryl) methyl] acrylic acid ethyl esters 6.

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