892875-81-9Relevant articles and documents
Using experimental and computational approaches to probe an unusual carbon-carbon bond cleavage observed in the synthesis of benzimidazole: N -oxides
Politano, Fabrizio,Sandoval, Arturo León,Uranga, Jorge G.,Buján, Elba I.,Leadbeater, Nicholas E.
supporting information, p. 208 - 215 (2021/01/14)
Experimental and computational studies have been performed in order to investigate an unusual carbon-carbon bond cleavage that occurs in the preparation of certain benzimidazole N-oxides from anilines. The key factor determining the outcome of the reactio
From N-(dinitrophenyl) amino acids to benzimidazole N-oxides. Synthesis, kinetics and mechanism
Bujan, Elba I.,Salum, Maria Laura
, p. 187 - 195 (2007/10/03)
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 α- and β-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 kN=1.7 × 10-3 M-1 S-1. The mechanism proposed includes the formation of an N-alkylidene 2-nitrosoaniline-type intermediate as the rate-determining step. Copyright
