PREPARATION AND SOME PROPERTIES OF 2H-IMIDAZOLE 1,3-DIOXIDES, DERIVATIVES OF ALICYCLIC 1,2-DIOXIMES

Article abstract of DOI:10.1007/PL00020454

The corresponding 2H-imidazole 1,3-dioxides were obtained by the reaction of cyclohexanedione and cycloheptanedione 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 bromineatoms 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.