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Short Paper | Regular issue | Vol 96, No. 10, 2018, pp.1771-1778
Published online, 26th September, 2018
DOI: 10.3987/COM-18-13966
One-Pot Synthesis of 3-Oxo-2H,4H-1,4-benzothiazine-2-carbonitrile Derivatives via Cyclization of Methyl {[2-(Cyanomethyl)sulfanyl]phenyl}carbamate

Kazuhiro Kobayashi,* Kazuki Kawano, and Daiki Fujiwara

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

Abstract

A facile method for the synthesis of 3-oxo-2H,4H-1,4-benzothiazine-2-carbonitrile (2-cyano-2H-1,4-benzothiazin-3(4H)-one) derivatives has been developed. Sodium hydride-mediated cyclization of methyl {[2-(cyanomethyl)sulfanyl]phenyl}carbamate, which can be easily prepared from commercially available 2-aminobenzenethiol in two steps, allows the synthesis of 3-oxo-2H,4H-1,4-benzothiazine-2-carbonitrile and its 2-mono- and 2,4-di- alkylated derivatives in one-pot.