Unexpected formation of imidazole-4,5-dicarboxylic acid in the oxidation of 2-substituted benzimidazoles with hydrogen peroxide

Abstract

SHORT COMMUNICATIONSThe unique structure of imidazole-4,5-dicarboxylic acid (4,5-IDC) and its 2-alkyl derivatives, specifically the presence of six heteroatoms in a single molecule and the ability to lose one to three protons with formation of the corresponding anions, gives rise to a variety of coordination modes in their complexes with transition metal ions [1-3] and determines the use of 4,5-IDC derivatives in different fields of chemistry such as catalysis [1] and gas separation and adsorption [2]. On the other hand, 4,5-IDC derivatives are interesting for pharmacology [4][5][6]. Amides derived from 4,5-IDC stimulate the central nervous system and exhibit antiproliferative activity [5], while 2-alkyl-substituted derivatives are NMDA receptor ligands [6].