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Short Paper | Regular issue | Vol 94, No. 6, 2017, pp.1152-1158
Published online, 18th April, 2017
DOI: 10.3987/COM-17-13698
Synthesis of 3-Iminobenzo[c]thiophen-1(3H)-one Derivatives Based on the Reaction of 2-Lithio-N,N-dimethylbenzamides with Isothiocyanates

Kazuhiro Kobayashi,* Yuuho Shigemura, and Daiki Fujiwara

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


A facile two-step sequence for the preparation of 3-(Z)-(aryl(or alkyl)imino)benzo[c]thiophen-1(3H)-ones starting from 2-bromo-N,N- dimethylbenzamides has been developed. The starting amides were allowed to react with butyllithium to generate 2-lithio-N,N-dimethylbenzamides, of which reaction with isothiocyanates gave the corresponding N,N-dimethyl-2-(thiocarbamoyl)benzamides. These precursors were treated with p-toluenesulfonic acid monohydrate. The cyclization proceeds in a chemo- and stereo-selective manner to provide the desired product as the sole isolated product in each case.