ChemInform Abstract: Structural Reorganization of Allyl Isothiocyanate into Pyrrole Ring under Superbase: A Straightforward Access to NH-2-(Alkylsulfanyl)-1H-pyrroles and N-Alkyl-2-(alkylsulfanyl)-1H-pyrroles

A novel and facile synthetic route to NH-2-(alkylsulfanyl)-1 H -pyrroles and N -alkyl-2-(alkylsulfanyl)-1 H -pyrroles is reported. This was achieved by deprotonation of allyl isothiocyanate with the superbasic pair lithium diisopropylamide and potassium tert -butoxide (1:1 molar mixture), followed by intramolecular ring closure, deprotonation of cyclic anion with a second equivalent of the superbase, and final sequential N-protolysis/S-alkylation or N,S-dialkylation of the formed N,S-centered pyrrol-2-ylsulfide dianion.