Synthesis of 2‑Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C–C Bond Cleavage of 2‑Arylindoles

A variety of 2-aminobenzonitriles were prepared from 2-arylindoles in good to excellent yields through tert-butylnitrite (TBN)-mediated nitrosation and sequential iron­(III)-catalyzed C–C Bond cleavage in a one-pot fashion. The 2-aminobenzonitriles can be used to rapidly synthesize benzoxazinones by intramolecular condensation. The present method features an inexpensive iron­(III) catalyst, gram scalable preparations, and novel C–C bond cleavage of indoles.