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Paper | Regular issue | Vol 87, No. 12, 2013, pp.2533-2553
Published online, 1st November, 2013
DOI: 10.3987/COM-13-12838
4-Trifluoroacetyl-2-phenyloxazol-5-one: Versatile Template for Synthesis of Trifluoromethyl-Substituted Heterocycles

Ryosuke Saijo, Ken-ichi Kurihara, and Masami Kawase*

*Faculty of Pharmaceutical Sciences, Matsuyama University, 4-2 Bunkyo-cho, Matsuyama, Ehime 790-8578, Japan

Abstract

4-Trifluoroacetyl-2-phenyloxazol-5-one (1) is a versatile template for the synthesis of various trifluoromethyl-substituted heterocycles. Cyclocondesation of 1 with hydroxylamine and hydrazine afforded isoxazole and pyrazole, respectively. Another key protocol involves nucleophilic ring opening of 1 with H2O or MeOH to give α-amido trifluoromethylketones which are transformed into trifluoromethyl-substituted thiazoles, oxazoles, imidazoles, pyrazoles, and pyrimidines.