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Short Paper | Regular issue | Vol 92, No. 12, 2016, pp.2225-2234
Published online, 8th November, 2016
DOI: 10.3987/COM-16-13566
An Efficient Synthesis of 3-(Arylsulfanyl)quinolin-4(1H)-ones via Cyclization of N-{2-[2-(Arylsulfanyl)acetyl]phenyl}benzamides with N,N-Dimethylformamide Dimethyl Acetal

Kazuhiro Kobayashi,* Kohei Nishikawa, and Takashi Nogi

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

Abstract

The reaction of N-[2-(2-chloroacetyl)phenyl]benzamides, readily derived from 2-(2,2-dichloroethenyl)benzenamines, with sodium arenethiolates gives the corresponding N-{2-[2-(arylsulfanyl)acetyl]phenyl}benzamides. These are treated with N,N-dimethylformaide dimethyl acetal (DMF–DMA) to yield 3-(arylsulfanyl)quinolin-4(1H)-ones in generally good yields.