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Note | Regular issue | Vol 75, No. 10, 2008, pp.2555-2562
Published online, 12th June, 2008
DOI: 10.3987/COM-08-11425
Synthesis of 1(3H)-Iminobenzo[c]thiophene Derivatives by Hydriodic Acid-Mediated Cyclization of 2-(Vinyl)thiobenzamide Derivatives

Kazuhiro Kobayashi,* Seiki Fujita, and Hisatoshi Konishi

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

Abstract

Secondary 2-(vinyl)thiobenzamide derivatives, easily prepared by reacting 2-lithiostyrene derivatives with various isothiocyanates, undergo intramolecular cyclization on treatment with concentrated hydriodic acid to produce 1(3H)-iminobenzo[c]thiophene derivatives in fair-to-good yields. Some of them have been hydrolyzed under acidic conditions to afford benzo[c]thiophen-1(3H)-one derivatives in good yields.