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Thermolysis of [1,2,4]triazolo[1,5-a]pyrimidine n-ylides
Authors:Mikio Hori  Kiyomi Tanaka  Tadashi Kataoka  Hiroshi Shimizu  Eiji Imai  Kazuhiko Kimura  Yoshinobu Hashimoto
Affiliation:Gifu Pharmaceutical University, 6-1, Mitahora-higashi 5-chome, Gifu 502, Japan;Kaken Pharmaceutical Co., Ltd., 2-28-8, Honkomagome, Bunkyo-ku, Tokyo 113, Japan
Abstract:5,7-Dimethyl[1,2,4]triazolo[1,5-a]pyrimidinio-3-phenacylide (3) generated by the reaction of an iminium salt (2) with 1 eq. of triethylamine, underwent a new thermal ring cleavage of the triazole moiety to give the pyrimidine derivative. However reaction of 2 with 2 eq. of triethylamine afforded the 2-iminooxazoline derivative. The iminooxazoline reacted with nucleophiles such as alcohols or amines to give imidazoles.
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