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Short Paper | Regular issue | Vol 94, No. 12, 2017, pp.2273-2290
Published online, 1st November, 2017
DOI: 10.3987/COM-17-13791
One-Pot, Diversity-Oriented Synthesis of Aryl-Substituted Benzoxacycles Including Benzofuran, Coumarin, and Benzoxazepine

Hisashi Masui, Eri Ohkawa, Rika Kitahara, Kiyofumi Wanibuchi, and Takashi Takahashi*

*Department of Pharmaceutical Sciences, Yokohama University of Pharmacy, 601 Matano-cho, Totsuka-ku, Yokohama 245-0066, Japan


A one-pot method for the synthesis of benzoxacycles including benzofuran, coumarin, benzoxazepine, and benzoxazocine from a common synthetic intermediate was established. Benzoxacycles are privileged structures in medicinal chemistry and have featured in several clinically used drugs. The synthesis of a benzofuran containing an aryl substituent was accomplished using potassium carbonate and sodium hydride. The one-pot synthesis of coumarin was also carried out using trans-decalin as the solvent. The optimized conditions for the one-pot synthesis of benzoxazepine can also be applied to the synthesis of benzoxazocine.