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Communication | Regular issue | Vol 75, No. 1, 2008, pp.35-42
Published online, 2nd October, 2007
DOI: 10.3987/COM-07-11195
Electrooxidative Cyclization of Benzylideneaminothiophenols to the Corresponding 2-Arylbenzothiazoles

Mitsuhiro Okimoto,* Takashi Yoshida, Masayuki Hoshi, Kazuyuki Hattori, Masashi Komata, Kenta Tomozawa, and Tomohito Chiba

*Department of Applied and Environmental Chemistry, Kitami Institute of Technology, Koen-cho 165, Kitami, Hokkaido 090-8507, Japan

Abstract

Several benzylideneaminothiophenols were electrochemically oxidized in methanol containing sodium acetate as the supporting electrolyte, to afford the corresponding 2-arylbenzothiazols. The reaction proceeded via intramolecular cyclization involving the formation of a new bond between the benzylic carbon of the substrate and the sulfur of the thiol group. Based on the yields, room temperature and the use of two equivalents of sodium acetate relative to the substrate as the supporting electrolyte were found to be the optimal reaction conditions. The electrooxidation presumably involves a two-electron oxidation process.