2,2′-Bi(1H-indolyl)-3,3′-dicarbaldehydes, prepared from lH-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.