Science and Technology Production
Article
Authorship
Date
2006
Publishing House and Editing Place
John Wiley & Sons, Ltd
Magazine
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY,
vol. 19
(pp. 187-195)
John Wiley & Sons, Ltd
Summary
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SIGEVA
Several benzimidazole N-oxide derivatives were synthesized in very good yields by heating under reflux the corresponding N-(2,4- or 2,6-dinitrophenyl) amino acid derivative with NaOH in 60% 1,4-dioxane?H2O. The N-oxides obtained from glycine and - and -alanine derivatives lost the carboxylic group. The observed rate constant for the reaction of N-(2,4-dinitrophenyl) glycine (2a) in 10% 1,4-dioxane?H2O to give 5-nitro-1H-benzimidazole-3-oxide (4a) is first order on [NaOH]; the second-order rate ...
Several benzimidazole N-oxide derivatives were synthesized in very good yields by heating under reflux the corresponding N-(2,4- or 2,6-dinitrophenyl) amino acid derivative with NaOH in 60% 1,4-dioxane?H2O. The N-oxides obtained from glycine and - and -alanine derivatives lost the carboxylic group. The observed rate constant for the reaction of N-(2,4-dinitrophenyl) glycine (2a) in 10% 1,4-dioxane?H2O to give 5-nitro-1H-benzimidazole-3-oxide (4a) is first order on [NaOH]; the second-order rate constant is kN¼1.7103 M1 s1. The mechanism proposed includes the formation of an N-alkylidene 2-nitrosoaniline-type intermediate as the rate-determining step.
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Key Words
SYNTHESISBENZIMIDAZOLE N-OXIDEN-(DINITROPHENYL) AMINO ACIDSMECHANISM