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Communication | Regular issue | Vol 24, No. 10, 1986, pp.2735-2738
Published online, 1st January, 1970
DOI: 10.3987/R-1986-10-2735
Anomalous Witting Reaction of Aldonic Thioamide Derivatives. A New Mode of Thiazole Ring Formation

László Somogyi,* Pál Herczegh, and Gyula Batta

*Reseaech Group of Antibiotics, Hungarian Academy of Sciences, H-4010 Debrecen, Hungary

Abstract

A new mode of thiazole ring formation and an unexpected acetoxy group elimination were observed as a result of the reaction of N-acetyl-per-O-acetylhexonic thioamides (1b and 2b) with ethoxycarbonylmethylenetriphenylphosphorane affording ethyl 2-(1’,5’-diacetoxy-penta-1’,3’-Z,E-dien-1’-yl)-4-methylthiazole-5-carboxylate (6).