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Paper | Regular issue | Vol 65, No. 9, 2005, pp.2119-2126
Published online, 22nd July, 2005
DOI: 10.3987/COM-05-10466
One-Pot Synthesis of 2-Aryl- and 2-Alkylbenzothiazoles under Microwave Irradiation

Sukanta Kamila, Hongming Zhang, and Edward R. Biehl*

*Chemistry Department, Southern Methodist University, Dallas, TX 75275-0314, U.S.A.

Abstract

Eco-friendly direct solvent-free reactions of o-aminothiophenol and aromatic or aliphatic β-keto esters with microwave irradiation produced 2-substituted benzothiazoles in excellent yield. Experiments that compared microwave irradiation to conventional heating methods showed that the former gives the 2-substituted benzothiazoles faster and in higher yields. The formation of the titled compounds probably involves the nucleophilic addition of the thiol group to the keto group of the β-keto ester with subsequent elimination of ethyl acetate from the resulting adduct. The adduct then undergoes an intramolecular addition of the o-amino group to the carbonyl group to give an adduct from which water is eliminated to afford the 2- substituted benzothiazoles.