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Paper | Regular issue | Vol 55, No. 11, 2001, pp.2131-2137
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9322
■ Convenient Preparation of Heteroazulenes by the Reaction of 2-Aminotropone with Heterocumulenes in the Presence of a Base

Yuhki Mitsumoto and Makoto Nitta*

*Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan

Abstract

Reactions of 2-aminotropone with heterocumulenes, N,N’-diphenylcarbodiimide, phenyl isothiocyanate, phenyl isocyanate, and carbon disulfide, in the presence of t-BuOK afforded 1-phenylcycloheptaimidazole-2(1H)-phenylimine, 1-phenylcyclohepataimidazole-2(1H)-thione, 1-phenylcycloheptaimidazol-2(1H)-one along with 2H-cycloheptaoxazol-2-one, and 2H-cycloheptathiazol-2-one along with 2H-cycloheptaoxazole-2-thione in good to moderate yields, respectively.