title: Product analyses of ozone mediated nitration of benzimidazole derivatives with nitrogen dioxide: formation of 1-nitrobenzimidazoles and conversion to benzotriazoles.
abstract: Several benzimidazole derivatives having electron-withdrawing or -donating substituent(s) at the benzene moiety were used as models of the imidazole moiety of purine bases and their nitration with nitrogen dioxide and ozone (so-called Kyodai nitration) were examined. Products were extracted from the reaction mixture with AcOEt and their structures were analyzed. 1-Nitrobenzimidazole derivatives and unexpected 1-nitrobenzotriazole derivatives were identified. Although the yields of 1-nitrobenzimidazole derivatives were quite low, these were all new compounds that could be obtained only by Kyodai nitration. It was speculated that benzotriazoles were formed via 1-nitrobenzimidazoles and subsequent nitration toward benzotriazoles resulted in the formation of 1-nitrobenzotriazoles.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Nagoya City University, Japan.
authors.forename: Toyo
authors.initials: T
authors.lastname: Kaiya
authors.forename: Kei
authors.initials: K
authors.lastname: Nakamura
authors.forename: Masaru
authors.initials: M
authors.lastname: Tanaka
authors.forename: Naoki
authors.initials: N
authors.lastname: Miyata
authors.forename: Kohfuku
authors.initials: K
authors.lastname: Kohda
mesh_terms: D001562:Benzimidazoles / Q000032:analysis* / Q000737:chemistry; D009566:Nitrates / Q000032:analysis / Q000737:chemistry; D009585:Nitrogen Dioxide / Q000032:analysis* / Q000737:chemistry; D010126:Ozone / Q000032:analysis* / Q000737:chemistry; D014230:Triazoles / Q000032:analysis* / Q000737:chemistry
chemical_list: D001562:Benzimidazoles; D009566:Nitrates; D014230:Triazoles; D010126:Ozone; C012771:benzotriazole; C031000:benzimidazole; D009585:Nitrogen Dioxide