Controllable synthesis of pyrido[2,3-b]indol-4-ones or indolo[3,2-b]quinolines via formal intramolecular C(sp2)–H functionalization

Abstract

A novel Fe-catalyzed protocol for the controllable synthesis of pyrido[2,3-b]indol-4-ones or indolo[3,2-b]quinolines has been developed by using indole-2-carboxylic derivatives as starting materials. Indole-2-carboxenamines were transformed into pyrido[2,3-b]indol-4-ones through intramolecular N–H/C–H coupling, in which a carbonyl 1,2-migration was involved. Whereas, when indole-2-carboxarylamines were employed, indolo[3,2-b]quinolones were produced through direct N–H/C–H coupling. The desired products were obtained under mild reaction conditions in moderate to good yields with wide substrate scope. The natural product quindolinone was conveniently prepared by this reaction.