V. Samsonov, L. B. Volodarskii
Jun 1, 1980
Citations
0
Influential Citations
4
Citations
Journal
Chemistry of Heterocyclic Compounds
Abstract
The corresponding 2H-imidazole 1,3-dioxides were obtained by the reaction of cyclohexanedione and cycloheptadione 1,2-dioximes with acetone, cyclopentanone, and methyl ethyl ketone. The reactions of these compounds with hydroxylamine hydrochloride, NaBH4, a Grignard reagent, and acetic anhydride in the presence of H2SO4 were studied in the case of 2,2-dimethyl-4,5,6,7-tetrahydro-2H-benzimidazole 1,3-dioxide. Bromination of the latter and 2,2-dimethylcyclohepta-2H-imidazole 1,3-dioxide with N-bromosuccinimide gave the corresponding dibromo derivatives, the bromine atoms in which are replaced by acetoxy and hydroxy groups. 4,7-Dihydroxy-2, 2-dimethyl-4,5,6,7-tetrahydro-2H-benzimidazole 1,3-dioxide, which was obtained by oxidation with MnO2 was converted to a quinone, viz., 2,2-dimethyl-4,7-dioxo-4,7-dihydro-2H-benzimidazole 1,3-dioxide.