Syntheses of condensed imidazoles by lead tetraacetate oxidation of amidines

Article abstract of DOI:10.1139/v82-167

2-Phenylbenzimidazoles, 2-benzylbenzimidazoles, 2-phenyl-1H-naphthol<1,2-d>imidazole, and 2-benzyl-1H-naphthol<1,2-d>imidazole have been synthesized in excellent yields (77-98percent) by lead tetraacetate oxidation of suitable N-arylbenzimides, N-arylphenylacetamidines, N-α-naphthylbenzimidine, and N-α-naphthylphenylacetamidine respectively.The mechanism of nitrene insertation and intramolecular competitive nitrene insertation leading to these heterocycles has also been discussed.