An efficient synthetic route to biologically relevant 2-phenylbenzothiazoles substituted on the benzothiazole ring

Abstract

Certain 2-phenylbenzothiazoles containing substituents on the benzothiazole ring possess important biological properties, yet the majority of synthetic methods to 2-phenylbenzothiazoles described to date focus on their unsubstituted ring counterparts. Here we describe a new concise and efficient synthetic route to biologically relevant 2-phenylbenzothiazoles in high yield from the reaction of substituted 2-aminothiophenol disulfides and benzaldehydes, promoted by the inexpensive and non-toxic inorganic oxidant sodium metabisulfite in DMSO at 120 °C. Our new method is tolerant of a range of substituents on both the benzothiazole and phenyl ring, and affords efficient access to substituted 2-phenylbenzothiazoles without the need for column chromatography.