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Paper | Regular issue | Vol 92, No. 5, 2016, pp.844-856
Published online, 10th March, 2016
DOI: 10.3987/COM-16-13421
Synthesis of N,N-Disubstituted 1-Aryl-1,3-dihydro-2H-isoindole-2-carbothioamides

Kazuhiro Kobayashi,* Yuuho Shigemura, and Miyuki Tanmatsu

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

Abstract

A convenient method for the synthesis of N,N-disubstituted 1-aryl-1,3-dihydro-2H-isoindole-2-carbothioamides starting from 2-[aryl(methoxy)methyl]phenyl bromides is described. Thus, the reaction of 1-[aryl(methoxy)methyl]-2-(isothiocyanatomethyl)benzenes, derived from the starting materials by an easily operated five-step sequence under mild conditions, with secondary amines provides the corresponding thiourea derivatives, which cyclize on treatment with methanesulfonic acid to afford the desired products.