Conversion of thiobenzamides to benzothiazoles via intramolecular cyclization of the aryl radical cation

Article abstract of DOI:10.1016/j.tet.2008.06.023

A new and general method has been developed for the intramolecular cyclization of thiobenzamides to benzothiazoles via aryl radical cations as reactive intermediates. The method utilizes phenyliodine(III) bis(trifluoroacetate) (PIFA) in trifluoroethanol or cerium ammonium nitrate (CAN) in aqueous acetonitrile at room temperature to effect cyclization within 30 min in moderate yields.