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DFT investigations are carried out to improve the domino cyclization between gem-dialkylthio vinylallenes and benzylamine.Economic reaction approaches were explored,namely,this reaction can occur under organic solvent-free conditions either catalyzed by trace water or self-catalyzed by BnNH2.Three types of reactions(DMSO-assisted,trace water-catalyzed,and self-catalyzed by BnNH2)shared the same reaction mechanism with the nucleophilic attack of BnNH2 to the allenic carbon of thioamide intermediate Re.For trace water-catalyzed reaction another mechanism was also found that is the BnNH2 attacks the carbonyl carbon of the conformational isomer of Re.Among the investigated mechanisms,the trace water-catalyzed one is suggested to be the most efficient and convenient synthetic method for pyrroles.Our calculated results were further confirmed by the experimental observation,which opens a new strategy for the synthesis of pyrroles.