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Short Paper | Special issue | Vol 86, No. 2, 2012, pp.1661-1674
Published online, 22nd November, 2012
DOI: 10.3987/COM-12-S(N)121
Synthesis of a Library of 1,5,2-Dithiazepine 1,1-Dioxides. Part 1: A One-Pot Sulfonylation/Thia-Michael Protocol

Qin Zang, Aihua Zhou, Salim Javed, Pradip K. Maity, Chirs A. Knudtson, Danse Bi, Jared J. Hastings, Fatima Z. Basha, and Paul R. Hanson*

*5029 Malott Hall, Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr., Lawrence
Kansas 66045-7582, U.S.A.

Abstract

A novel one-pot sulfonylation/intramolecular thia-Michael protocol is reported for the synthesis of 1,5,2-dithiazepine 1,1-dioxides. Sulfonylation between cysteine ethyl ester/cysteamine and 2-chloroethanesulfonyl chloride, followed by in situ intramolecular thia-Michael addition, was achieved and afforded the titled 1,5,2-dithiazepine-1,1-dioxide scaffolds. Diversification was demonstrated for future library synthesis.