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Paper | Special issue | Vol 37, No. 1, 1994, pp.441-459
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S32
Generation of the Dihydro-5H-Thiazolo[3,2-a]pyridin-3-one Ring System by Proton Loss from Isothiomünchnones

Albert Padwa* and Zhijia J. Zhang

*Department of Chemistry, Emory University, 1515 Pierce Drive Atlanta, Georgia 30322, U.S.A.

Abstract

Dihydro-5H-thiazolo[3,2-a]pyridin-3-ones are easily generated by proton loss from isothiomÜnchnones. The closely related tetrahydro-2H-pyrido[2,1-b][1,3]thiazin-4-one ring system was prepared by heating piperidine-2-thione with acryloyl chloride. These cyclic S,N-ketene acetals undergo smooth reaction with different electrophiles in the presence of Lewis acids.