title: Carbene-mediated transformations of 1-(benzylideneamino)benzimidazoles.
abstract: Carbene-mediated transformations of N-(3-butylbenzimidazol-3-ium-1-yl)-1-arylmethanimine iodides with carbon disulfide and benzoyl isothiocyanate gave the corresponding NHC·CS(2) betaines in 68-85% and benzoyl-[1-butyl-3-[(E)-(aryl)methyleneamino]benzimidazol-1-ium-2-carbothioyl]azanides, respectively, in 74-85% yields. However, reaction with excess isopropyl isothiocyanate in NaH/THF at room temperature yielded the 1-butyl-1',3'-diisopropyl-3-[(E)-(aryl)methyleneamino]spiro[benzimidazole-2,5'-imidazolidine]-2',4'-dithiones (74-77%).
authors.affiliation: Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, United States. katritzky@chem.ufl.edu
authors.forename: Alan R
authors.initials: AR
authors.lastname: Katritzky
authors.forename: Davit
authors.initials: D
authors.lastname: Jishkariani
authors.forename: Rajeev
authors.initials: R
authors.lastname: Sakhuja
authors.forename: C Dennis
authors.initials: CD
authors.lastname: Hall
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Steel
mesh_terms: D001562:Benzimidazoles / Q000737:chemistry*; D002384:Catalysis; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D001562:Benzimidazoles; C030011:carbene; D008697:Methane