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Synthesis 2007(5): 709-712  
DOI: 10.1055/s-2007-965912
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Functionalized Sulfonamides via Multicomponent Reaction of Alkyl Isocyanide and Dialkyl Acetylenedicarboxylate with 4-Methylbenzenesulfonic Acid Monohydrate

Abdolali Alizadeh*a, Sadegh Rostamniaa, Abbas Ali Esmailib
a Department of Chemistry, Tarbiat Modarres University, P.O. Box 14115-175, Tehran, Iran
b Department of Chemistry, University of Birjand, P.O. Box 97175-615, Birjand, Iran
Fax: +98(21)88006544; e-Mail: abdol_alizad@yahoo.com; e-Mail: aalizadeh@modares.ac.ir;
Further Information

Publication History

Received 25 October 2006
Publication Date:
25 January 2007 (online)

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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.

Key words

alkyl isocyanide - dialkyl acetylenedicarboxylate - 4-methylbenzenesulfonic acid monohydrate - multicomponent reaction

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