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Paper | Regular issue | Vol 91, No. 9, 2015, pp.1723-1734
Published online, 24th August, 2015
DOI: 10.3987/COM-15-13256
Metal-Free Synthesis of Benzothiazoles from Disulfides of 2-Aminobenzenethiol and Carboxylic Acid via PCl3-Promoted Tandem Reaction

Guangyan Du, Ning Zhu,* Limin Han, Hailong Hong, and Quanling Suo

*Chemical Engineering College, Inner Mongolia University of Technology, Hohhot 010051, China

Abstract

A metal-free process for the synthesis of benzothiazoles via PCl3-promoted cleavage/acylation/ cyclization of disulfides and carboxylic acids has been developed. In addition to acting as the acylating reagent which converted carboxylic acids into acyl chlorides, PCl3 also converted disulfides to thiols, which promoted disulfides of 2-aminobenzenethiol reacted with carboxylic acid to produce benzothiazoles. The developed method is applicable to a wide range of carboxylic acids containing different functional groups.