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Communication | Special issue | Vol 61, No. 1, 2003, pp.65-68
Published online, 2nd October, 2003
DOI: 10.3987/COM-03-S38
Novel Synthesis of Azocine, Azepine, Oxocine, and Oxepine Derivatives by Palladium-catalyzed Medium-Ring Formation from Bromoallenes

Hiroaki Ohno,* Hisao Hamaguchi, Miyo Ohata, Shohei Kosaka, and Tetsuaki Tanaka*

*Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan

Abstract

Novel and efficient synthesis of medium-sized heterocycles such as azepine, oxepine, and benzo[d]azocine derivatives is described. Treatment of bromoallenes having a nucleophilic moiety with sodium alkoxide and a palladium(0) catalyst in the presence of an alcohol leads to regioselective formation of medium-sized rings at the central position of the allenic carbon.