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Short Paper | Regular issue | Vol 96, No. 11, 2018, pp.1966-1976
Published online, 18th October, 2018
DOI: 10.3987/COM-18-13986
Synthesis of 4-Arylisoquinoline-1(2H)-thione Derivatives by Sodium Hydride-Mediated Cyclizations of 2-(1-Arylethenyl)benzothioamides

Kazuhiro Kobayashi* and Takuma Ueyama

*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


A new and facile method for the general preparation of isoquinoline-1(2H)-thione derivatives has been developed. Thus, the sodium hydride-mediated cyclization of N-substituted 2-(1-arylethenyl)benzothioamides, which are derived from the reaction of 2-(1-arylethenyl)phenyllithiums with isothiocyanates, gives 2-substituted 4-aryl-3,4-dihydroisoquinoline-1(2H)-thiones. In addition, the use of N-substituted 2-(1-aryl-2-methoxyethenyl)benzothioamides from 2-(1-aryl-2-methoxyethenyl)phenyllithiums and isothiocyanates affording 2-substituted 4-arylisoquinoline-1(2H)-thiones is described.