2, 2′-Bi (1H-indolyl)-3, 3′-dicarbaldehydes, prepared from 1H-indole-3-carbaldehydes by exploiting SET methodology, served as the key compound for synthesizing indolo [2, 3-a] carbazoles as well as nitrogen macroheterocycles. Condensation of 2, 2′-bi (1H-indolyl)-3, 3′-dicarbaldehyde with aliphatic diamines produced Schiff's base type compounds possessing a 10–14-membered ring.