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Paper | Regular issue | Vol 24, No. 9, 1986, pp.2563-2570
Published online, 1st January, 1970
DOI: 10.3987/R-1986-09-2563
Ylide-induced Ylide Formation: A Thermal Reaction and a Double Cycloaddition Reaction of [1,2,4]Triazolo[1,5-a]pyridinium Ylides

Mikio Hori,* Tadashi Kataoka, Hiroshi Shimizu, Eiji Imai, Masaharu Yokomoto, Kiyomi Tanaka, Kazuhiko Kimura, and Yoshinobu Hashimoto

*Department of Pharmacognosy, Gifu College of Pharmacy, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan

Abstract

1-Alkyl[1,2,4]triazolo[1,5-a]pyridinium salts (2) were synthesized by the reaction of [1,2,4]triazolo[1,5-a]pyridine (1) with alkyl halides in dry acetone under reflux. The thermal reaction of ylides (3) gave 2-cyanamidopyridines (4) or 2-oxazolylpyridine (5). The reaction of ylides (3) with methyl propiolate or dimethyl acetylenedicarboxylate resulted in the formation of pyrazolo[1,5-a]pyridine derivatives via a double 1,3-dipolar cycloaddition reaction.