Quinolines (2 and 3) and naphthazepines (8 and 9) are prepared in high yields by the reaction of tris(isopropylthio)cyclopropenylium perchlorate (1) with anilines and 1-naphthylamines, respectively, under nitrogen in N,N-dimethylformamide at 80-85-degrees-C. The reactions are proven to proceed through the intermediary formation of iminium salts (5, 10, and 11) derived from 1 and amines. The reaction of 1 with pyrrole and indole in dimethyl sulfoxide, containing sodium hydride, at 25-degrees-C gives 5,6,7-tris(isopropylthio)-1H-pyrrolizine (12) and 1,2,3-tris(isopropylthio)-9H-fluorazene (14), respectively, in high yields by intramolecular cyclization of a vinylcarbene intermediate. The possible pathway for the formation of these nitrogen heterocycles is proposed.
