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Paper | Regular issue | Vol 78, No. 1, 2009, pp.169-176
Published online, 8th September, 2008
DOI: 10.3987/COM-08-11514
Synthesis of 2-Benzothiophene-1(3H)-thione and Isothiochromene-1-thione Derivatives by Iodine-mediated Cyclization of Lithium 2-(Vinyl)dithiobenzoate Derivatives

Shuhei Fukamachi, Hisatoshi Konishi, and Kazuhiro Kobayashi*

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

Abstract

Successive treatment of α-substituted 2-bromostyrenes with butyllithium and carbon disulfide generates lithium 2-(vinyl)dithiobenzoates, which are then allowed to react with iodine to give 3-substituted 3-iodomethyl-2-benzothiophene-1(3H)-thiones and/or 4-substituted isothiochromene-1-thiones in one-pot. Some of the former products can be transformed into the corresponding latter products on treatment with sodium hydrogencarbonate in refluxing acetonitrile.