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Paper | Regular issue | Vol 45, No. 4, 1997, pp.773-778
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7749
New Ring Transformation Reaction of Imidazothiazole with Acetylenic Acid Esters

Dong Chan Kim, Dong Jin Kim, Kye Jung Shin, Sang Woo Park*, and Kyung Ho Yoo*

*Biochemicals Research Center, Division of Applied Science, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 130-650, Korea

Abstract

3-Phenyl-5,6-dihydroimidazo[2,1-b]thiazole (1) as a nucleophile reacted with acetylenic acid esters such as ethyl propiolate and dimethyl acetylenedicarboxylate to give the new ring transformation compounds (2-oxo-imidazoline-1-yl)acrylic acid ethyl esters (6a-b) and [2-oxo-imidazoline-1-yl]but-2-enedioic acid diethyl esters (7a-b), respectively. Similarly, treatment of reactive imidazo[2,1-b]thiazolium betaines (3a-b) with acetylenic acid derivatives led to the corresponding ring transformation compounds. This reaction proceeded by the participation of water, and the resulting compounds were obtained in a mixture of cis and trans isomers.