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, PradipK Maity, ChrisA Knudtson, Danse Bi, JaredJ Hastings, FatimaZ Basha, PaulR Hanson

Index: Heterocycles 86(2) , doi:10.3987/COM-12-S(N)121, (2012)

Full Text: HTML

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.