A Novel Synthesis of Pyrroles by the Reactions of Tris(alkylthio)cyclopropenium Salt with Amines

One pot' synthesis of 2,3-bis(alky1thio)pyrroles in 45%80% yields under mild conditions was achieved by the reactions of tris(tert-buty1thio)cyclopropenium salt (1) with secondary "" amines in the presence of t-BuOK in DMF.Although the reaction of 1 with primary amine such as methylamine gave only the ring li opening product, the use of primary amines having structure of XCHZNHZ (X=CN, COOMe, Ph) resulted in the formation of the pyrroles bearing the substituent at the a-position in 44%71% yields.