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Communication | Regular issue | Vol 43, No. 6, 1996, pp.1179-1184
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7448
Intramolecular Reissert-Henze Reaction of Isoxazolo[2,3-a]pyridinium Salt; Facile Synthesis of Functionalized Phenacylpyridines from Ethynylpyridines

Nagatoshi Nishiwaki,* Masahiro Ariga, Mitsuo Komatsu, and Yoshiki Ohshiro

*Department of Chemistry, Osaka Kyoiku University, Asahigaoka 4-698-1, Kashiwara, Osaka 582, Japan

Abstract

Oxidation of 2-(phenylethynyl)pyridine with H2O2-AcOH gave isoxazolo[2,3-a]pyridinium acetate, which was successively attacked by alcohols in the presence of Na2CO3 to afford 6-alkoxy-substituted 2-phenacylpyridines in moderate yields. It was also possible to introduce amino or alkylthio functionality onto the pyridine ring by similar process. The present reaction is a new example of intramolecular Reissert-Henze-type reaction.