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Short Paper | Regular issue | Vol 83, No. 4, 2011, pp.883-889
Published online, 2nd March, 2011
DOI: 10.3987/COM-11-12142
One-Pot Synthesis of 4,5-Dihydro-3,1-benzoxazepine-2(1H)-thiones from 2-(2-Isocyanophenyl)ethanols via the Corresponding Isothiocyanates

Shuhei Fukamachi, Hisatoshi Konishi, and Kazuhiro Kobayashi*

*Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

An efficient method for the preparation of 4,5-dihydro-3,1-benzoxazepine-2(1H)-thiones under mild conditions has been developed. 2-(2-Isocyanophenyl)ethanols, easily accessible by treating 1-isocyano-2-(lithiomethyl)benzenes with aldehydes or ketones, were converted into the corresponding isothiocyanates on treatment with sulfur in the presence of a catalytic amount of selenium and excess triethylamine. These isothiocyanato alcohols were then treated with sodium hydride to give 4,5-dihydro-3,1-benzoxazepine-2(1H)-thione derivatives in one pot.