title: Synthesis and direct C2 functionalization of imidazolium and 1,2,4-triazolium N-imides.
abstract: Pd-catalyzed direct C2 arylation and Cu-catalyzed direct one-pot alkynylation/intramolecular cyclization of azolium N-imides are reported. Various acetylenes, aryl iodides, and 1-alkyl substituents were examined. The mild protocol allows direct C2 arylation of azolium N-imides without the use of specialized reagents together with novel one-pot regioselective preparations of imidazole-pyrazolo and pyrazolo-1,2,4-triazole ring systems. The electronic properties of selected examples were examined by fluorescence spectroscopy.
authors.affiliation: Center for Heterocyclic Compounds, Department of Chemistry, University of Florida , Gainesville, Florida 32611-7200, United States.
authors.forename: Deepak S
authors.initials: DS
authors.lastname: Panmand
authors.forename: Davit
authors.initials: D
authors.lastname: Jishkariani
authors.forename: C Dennis
authors.initials: CD
authors.lastname: Hall
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Steel
authors.forename: Abdullah M
authors.initials: AM
authors.lastname: Asiri
authors.forename: Alan R
authors.initials: AR
authors.lastname: Katritzky
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007094:Imides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007093:Imidazoles; D007094:Imides; D011720:Pyrazoles; D014230:Triazoles; D010165:Palladium; D003300:Copper