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The development of versatile new routes to bridgehead nitrogen-bearing polycyclic aromatic systems having privileged scaffolds is a synthetic challenge for organic chemists. An efficient synthesis of benzo[4,5]imidazo[1,2- a ]quinazoline derivatives bearing bridgehead nitrogen by the reaction of benzo[ d ]imidazol-2-amines, aldehydes, and  ortho -silyl aryltriflate  via  1,4-dipolar cycloaddition is reported under the optimized reaction conditions. The methodology provides easy access to fused benzimidazolo-quinazolines by sequential C–N and C–C bond formation through a one-pot reaction.

polycyclic aromatic compounds

A Versatile New Approach to Bridgehead Nitrogen Bearing Benzimidazolo-Quinazoline Hybrids: Facile 1,4-Dipolar Cycloaddition of Benzyne and  N -(1 H -Benzo[ d ]Imidazol-2-yl)-1-Phenylmethanimines