Selective N–N or N–S bond cleavage of 1-trifluoromethyl benzotriazoles enables divergent synthesis of 1,2,4-benzotriazines and benzotriazoles

Abstract

A variety of 1,2,4-benzotriazines and benzotriazoles are conveniently and divergently synthesized via novel metal-free cascade reactions of 1-trifluoromethyl benzotriazoles with alkyl bromides. The LiOH-mediated cascade reactions initiated by N–N bond cleavage smoothly afforded the 1,2,4-benzotriazine derivatives, and N¹-alkylated benzotriazoles were selectively formed via Cs₂CO₃-mediated desulfonylative substitution based on N–S bond cleavage.