Product analyses of ozone mediated nitration of benzimidazole derivatives with nitrogen dioxide: formation of 1-nitrobenzimidazoles and conversion to benzotriazoles.
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.
Kaiya
Toyo
T
Graduate School of Pharmaceutical Sciences, Nagoya City University, Japan.
Nakamura
Kei
K
Tanaka
Masaru
M
Miyata
Naoki
N
Kohda
Kohfuku
K
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
D001562:Benzimidazoles; D009566:Nitrates; D014230:Triazoles; D010126:Ozone; C012771:benzotriazole; C031000:benzimidazole; D009585:Nitrogen Dioxide