An Activated Trifluoromethyl Group as a Synthon for 2-Substituted Benzothiazole and Benzoxazole

Abstract

Dianions derived from 2-mercaptoaniline and 2-hydroxyaniline are cyclized to 2-substituted benzothiazole and benzoxazole, respectively, in the reaction with ortho or para trifluoromethyl-substituted anilines and quinolinamines that involves the CF 3 group. The carbon atom of the CF 3 group becomes C-2 of the five-membered ring system. Synthesis of 3-trifluoromethylquinoline-4-amine and 5-trifluoromethylquinoline- 6-amine is also reported