Title : ( Synthesis of Functionalized Sulfonamides via Multicomponent Reaction of Alkyl Isocyanide and Dialkyl Acetylenedicarboxylate with 4-Methylbenzenesulfonic Acid Monohydrate )
Authors: Abdolali Alizadeh , Sadegh Rostamnia , Abbas Ali Esmaeili ,
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Abstract
Protonation of the reactive intermediates produced in the reaction between alkyl isocyanides and dialkyl acetylenedicarboxylates by 4-methylbenzenesulfonic acid monohydrate leads to vinylnitrilium cations, which undergo a nucleophilic reaction with the conjugate base of the 4-methylbenzenesulfonic acid to produce dialkyl (E)-2-((alkylimino){[(4-methylphenyl)sulfonyl]oxy}methyl) but-2-enedioates. These intermediates rearrange to dialkyl (E)- 2-({alkyl)[(4-methylphenyl)sulfonyl]amino}carbonyl)but-2-enedioate derivatives, which react with water to produce dialkyl 2- ({alkyl[(4-methylphenyl)sulfonyl]amino}carbonyl)-3-hydroxysuccinates.
Keywords
, alkyl isocyanide, dialkyl acetylenedicarboxylate, 4- methylbenzenesulfonic acid monohydrate, multicomponent reaction
@article{paperid:1025973,
author = {Abdolali Alizadeh and Sadegh Rostamnia and Esmaeili, Abbas Ali},
title = {Synthesis of Functionalized Sulfonamides via Multicomponent Reaction of Alkyl Isocyanide and Dialkyl Acetylenedicarboxylate with 4-Methylbenzenesulfonic Acid Monohydrate},
journal = {Synthesis},
year = {2007},
volume = {5},
number = {5},
month = {January},
issn = {0039-7881},
pages = {709--712},
numpages = {3},
keywords = {alkyl isocyanide; dialkyl acetylenedicarboxylate; 4-
methylbenzenesulfonic acid monohydrate; multicomponent reaction},
}
%0 Journal Article
%T Synthesis of Functionalized Sulfonamides via Multicomponent Reaction of Alkyl Isocyanide and Dialkyl Acetylenedicarboxylate with 4-Methylbenzenesulfonic Acid Monohydrate
%A Abdolali Alizadeh
%A Sadegh Rostamnia
%A Esmaeili, Abbas Ali
%J Synthesis
%@ 0039-7881
%D 2007
