Aromatic N-N exchange reactions of N,N-dimethylamino gem-difluorinated heterocycles. A convenient synthesis of new 5-imidazol-1-yl alpha,alpha-difluoroketones

Aromatic nucleophilic substitution reaction of N,N-dimethylamino alpha,alpha-difluoroketones 2 and 3 in anhydrous dimethylsulfoxide, with several tetramethylammonium salts of imidazole as nucleophiles including imidazole, benzimidazole, imidazole-2-carboxaldehyde, 2-(4'-methoxyphenyl)imidazole and 2-methyl-5-nitro imidazole proceeds under mild conditions to give the corresponding nitrogen-nitrogen exchanged products 4-12 in moderate to good yields. Copyright (C) 1996 Elsevier Science Ltd