Reinvestigation of reactions of thiazolium and benzothiazolium N-phenacylides with electron-deficient acetylenes

T Iwamura, M Kobayashi, T Ichikawa…

Index: Iwamura, Tatsunori; Kobayashi, Masahiro; Ichikawa, Takashi; Shimizu, Hiroshi; Kataoka, Tadashi Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 7 p. 629 - 635

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Citation Number: 2

Abstract

Reactions of thiazolium and benzothiazolium N-phenacylides with dimethyl acetylenedicarboxylate (DMAD) have been reexamined. The thiazolium N-phenacylides 5, generated in situ from 4-methyl-or 5-phenyl-3-phenacylthiazolium bromides 13 with triethylamine, reacted with DMAD in dry DMF to give the thiazole ring-opened products 15, in which two molecules of DMAD had been incorporated. The reactions when conducted ...