title: Catalyst-controlled divergence in cycloisomerisation reactions of N-propargyl-N-vinyl sulfonamides: gold-catalysed synthesis of 2-sulfonylmethyl pyrroles and dihydropyridines.
abstract: Gold-catalysed, divergent synthesis of 2-sulfonylmethyl pyrroles and dihydropyridines from N-propargyl-N-vinyl sulfonamides has been achieved. Echavarren's gold(I) catalyst promoted the formation of pyrrole derivatives whereas the combination of PPh3AuCl and AgSbF6 afforded dihydropyridines. The aza-enyne precursors for the cycloisomerisation reaction were prepared by a base-mediated formal vinylic substitution reaction of 2-bromoallyl sulfones.
authors.affiliation: Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500 007, India. rajeevmenon@iict.res.in.
authors.forename: Sridhar
authors.initials: S
authors.lastname: Undeela
authors.forename: Srinivas
authors.initials: S
authors.lastname: Thadkapally
authors.forename: Jagadeesh Babu
authors.initials: JB
authors.lastname: Nanubolu
authors.forename: Kiran Kumar
authors.initials: KK
authors.lastname: Singarapu
authors.forename: Rajeev S
authors.initials: RS
authors.lastname: Menon
mesh_terms: D002384:Catalysis; D003500:Cyclization; D004095:Dihydropyridines / Q000138:chemical synthesis*; D006046:Gold / Q000737:chemistry*; D007536:Isomerism; D011758:Pyrroles / Q000138:chemical synthesis*; D013449:Sulfonamides / Q000737:chemistry*; D013450:Sulfones / Q000138:chemical synthesis
chemical_list: D004095:Dihydropyridines; D011758:Pyrroles; D013449:Sulfonamides; D013450:Sulfones; D006046:Gold