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Note | Regular issue | Vol 57, No. 9, 2002, pp.1697-1704
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9540
Unexpected Formation of Pyrrolo[2,1-b]thiazoles by Rearrangement of α-Hydroxydihydro-1,4-thiazines

Hoh-Gyu Hahn,* Kee Dal Nam, and Heduck Mah

*Organic Chemistry Laboratory, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 136-791, Korea

Abstract

A new synthesis of pyrrolo[2,1-b]thiazoles (5) is described. Hydrolysis of acetoxy dihydro-1,4-thiazine (2) prepared by Pummerer reaction of dihydro-1,4-thiazine sulfoxide gave the intermediate α-hydroxy sulfide (4). Dehydration of 4 gave pyrrolo[2,1-b]thiazoles (5). The reaction mechanism for the formation of 5 including the intermediate thiol (6) is discussed.