8-Phenyl-13a-(Trifluoromethyl)-13aH-benzo[4,5]imidazo[1,2-a]chromeno[3,2-e]pyridine-6-Carbonitrile

A DABCO-catalyzed one-pot synthesis of a novel pentacyclic heterocycle featuring an unprecedented benzo[4,5]imidazo[1,2-a]chromeno[3,2-e]pyridine scaffold from 2-(cyanomethyl)benzimidazole and 3-trifluoroacetyl-4-phenyl-4H-chromene has been developed. This hybrid architecture merges three privileged pharmacophores – benzimidazole, chromene, and pyridine – into a rigid, nearly planar π-extended system decorated with trifluoromethyl and nitrile groups. The structure of 8-phenyl-13a-(trifluoromethyl)-13aH-benzo[4,5]imidazo[1,2-a]chromeno[3,2-e]pyridine-6-carbonitrile was unambiguously confirmed by NMR spectroscopy and X-ray diffraction analysis. A plausible mechanism involves Michael addition, hemiaminal formation, ring opening, recyclization, and oxidation.