Abstract Highly efficient syntheses of indolo [2, 1-a] isoquinolines, indolo [2, 1-a][2] benzazepines, pyrrolo [2, 1-a] isoquinolines and pyrrolo [1, 2-a] benzazepines in excellent yields have been achieved by the intramolecular photochemical cross-coupling reactions of 3-acyl-2-halo-N-(ω-arylalkyl) indoles and 2-chloro-N-(ω-arylalkyl) pyrrole-3-carbaldehydes in acetone. A new heterocyclic ring system–pyrrolo [1, 2-d][1, 4] benzoxazepine–has also ...