Tandem SN2-Michael reactions for the preparation of simple five-and six-membered-ring nitrogen and sulfur heterocycles

RA Bunce, CJ Peeples, PB Jones

Index: Bunce, Richard A.; Peeples, Christopher J.; Jones, Paul B. Journal of Organic Chemistry, 1992 , vol. 57, # 6 p. 1727 - 1733

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Citation Number: 72

Abstract

A one-pot tandem SN2-Michael addition sequence has been developed for the preparation of five-memberedand six-membered-ring nitrogen and sulfur heterocycles from 6-or 7-halo-2- alkenoate esters. Nitrogen-containing rings are prepared by reaction of the w-halo-2- alkenoate eater with a primary amine in the presence of triethylamine. The sulfur analogues are generated by thiourea displacement of the halide followed by base hydrolysis of the ...