Dimethyl sulfoxide (DMSO) is one of the most commonly applied organic solvents in many organic reactions. It is known that DMSO/SOCl 2 is the e cient system for the intramolecular cyclization of 2alkenylanilines. The interaction of N-tosyl derivatives of 2-(cyclo)(alken-2-yl)-and 2-(cyclo)(alken-1yl)anilines with thionyl chloride was studied in the DMSO/SOCl 2 system. It was established that the structure of the obtained products depends on the structure of the alenyl fragment and the reaction conditions. As a result of these reactions, methylsulfanyl(cyclo)alkyl products, indole, carbazole or oxazepine were formed. The structure of new compounds was con rmed by IR, heteronuclear NMR spectroscopy, high resolution mass spectrometry.