Synthesis of methyl 3-amino-4-aryl(or methyl)sulfonyl-2- thiophenecarboxylates from 3-alkoxy-2-aryl(or methyl)-sulfonylacrylonitriles

Chad E. Stephens, Matthew B. Price, J. Walter Sowell

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The synthesis of a series of methyl 3-amino-4-aryl(or methyl)sulfonylthiophene-2-carboxylates by reaction of 3-alkoxy-2-aryl(or methyl)sulfonylacrylonitriles with methyl thioglycolate in the presence of triethylamine is described. Hydrolysis/decarboxylation of the ester at the 2- position and acylation of the resulting amine represents a convenient route to 4-arylsulfonyl-3-carboxamidothiophenes. Attempted acylation of a title aminothiophene under standard conditions was unsuccessful.

Original languageEnglish (US)
Pages (from-to)659-665
Number of pages7
JournalJournal of Heterocyclic Chemistry
Volume36
Issue number3
DOIs
StatePublished - Jan 1 1999
Externally publishedYes

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Acylation
Amines
Hydrolysis
Esters
alkoxyl radical
methyl thioglycolate
triethylamine
Decarboxylation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of methyl 3-amino-4-aryl(or methyl)sulfonyl-2- thiophenecarboxylates from 3-alkoxy-2-aryl(or methyl)-sulfonylacrylonitriles. / Stephens, Chad E.; Price, Matthew B.; Sowell, J. Walter.

In: Journal of Heterocyclic Chemistry, Vol. 36, No. 3, 01.01.1999, p. 659-665.

Research output: Contribution to journalArticle

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