Practical Copper-Catalyzed Double N-Arylation of Cyclic Diaryliodoniums: Synthesis of 5H-Dibenzo[d, f][1,3]Diazepine, and Benzo[c]Cinnoline Derivatives

Abstract

An efficient access to novel families of 7-membered dibenzodiazepines and 6-membered benzo[c]cinnoline derivatives has been elaborated. The synthetic strategy is based on a copper-catalyzed double N-arylation of cyclic diaryliodoniums with imidamides and 4-substituted 1, 2, 4-triazoline-3, 5-diones (TADs) respectively under ambient reaction conditions. A mechanistic rationale for the double N-arylation is discussed.