Synthesis and Cyclization Reactions of 2-Amino-3-[(methoxycarbonyl)methylsulfonyl]pyrroles and Thiophene

Chad E. Stephens, J. Walter Sowell

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The title aminopyrroles and thiophene have been prepared by condensation of methyl (cyanomethylsulfonyl)acetate with various α-amino ketones or 2-mercaptoacetaldehyde, respectively. Subsequent cyclization of these compounds by reaction between the amine and activated methylene has led to various ester-substituted thiazine- and thiadiazine-based bicyclic derivatives. In addition, cyclization of the title compounds by intramolecular coupling of the amine and ester has led to the analogous bicyclic thiazin-3(2H)-ones. Attempted hydrolysis of the ester-substituted bicyclics to the corresponding carboxylic acids was unsuccessful.

Original languageEnglish (US)
Pages (from-to)933-938
Number of pages6
JournalJournal of Heterocyclic Chemistry
Volume35
Issue number4
DOIs
StatePublished - Jan 1 1998
Externally publishedYes

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Thiophenes
Pyrroles
Cyclization
Esters
Amines
Thiadiazines
Thiazines
Carboxylic Acids
Ketones
Condensation
Hydrolysis
Derivatives

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and Cyclization Reactions of 2-Amino-3-[(methoxycarbonyl)methylsulfonyl]pyrroles and Thiophene. / Stephens, Chad E.; Walter Sowell, J.

In: Journal of Heterocyclic Chemistry, Vol. 35, No. 4, 01.01.1998, p. 933-938.

Research output: Contribution to journalArticle

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