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Paper | Regular issue | Vol 94, No. 12, 2017, pp.2262-2272
Published online, 23rd October, 2017
DOI: 10.3987/COM-17-13817
■ Synthesis of Benzo[c]thiophen-1(3H)-imine and 2,3-Dihydro-1H-isoindole-1-thione Derivatives through Cyclizations of 2-(1-Hydroxyalkyl)benzothioamides

Kazuhiro Kobayashi* and Takashi Nogi

*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

The reaction of N-alkyl-2,N-dilithiobenzothioamides, generated by treating N-alkylbenzothioamides with two equivalents of butyllithium, with aldehydes gives the corresponding 2-(1-hydroxyalkyl)benzothioamides, which undergo cyclization on treatment with methanesulfonyl chloride in the presence of triethylamine to yield 3,N-disubstituted (Z)-benzo[c]thiophen-1(3H)-imines. 2,3-Disubstituted 2,3-dihydro-1H-isoindole-1-thiones are obtained by the reaction of the above hydroxy thioamides with two equivalents of sodium hydride followed by an equivalent of phenyl chloroformate.