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Short Paper | Regular issue | Vol 83, No. 11, 2011, pp.2589-2596
Published online, 7th September, 2011
DOI: 10.3987/COM-11-12311
One-Pot Synthesis of Benzothiazol-2-amines by Cyclization of the Adducts between 2-Iodophenyl Isothiocyanates and Amines under Metal-Free Conditions

Kazuhiro Kobayashi,* Akihiro Kobayashi, Kazuya Murahashi, and Shuhei Fukamachi

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

Abstract

A convenient one-pot procedure for the preparation of N-substituted and N,N-disubstituted benzothiazol-2-amines under metal-free conditions has been developed, which employs the reaction of 2-iodophenyl isothiocyanates with primary and secondary amines followed by cyclization of the resulting thiourea precursors on treatment with triethylamine under relatively mild reaction conditions (< 70 ˚C). The reactions using diamines, such as ethylenediamines or trimethylenediamine, under similar conditions, albeit at higher temperature (130 ˚C), have proved to enable us to obtain N,N’-bis(benzothiazol-2-yl)ethane(or propane)diamines.