Synthesis, structure elucidation and determination of acid dissociation constant, tautomerism of pyrido [1,2-a] benzimidazole-2,4-dione

Abstract

The first starting material, 1H-2-acetylbenzimidazole, 4, was synthesized by o-phenylenediamine, 1, and lactic acid solution, 2, in hydrochloric acid medium on the first step than, oxidation reaction was performed by CrO3 in acetic acid medium on the second step. The last starting material, ethyl 2-(2-acetylbenzimidazol-1-yl) acetate, 6, was synthesized by using first starting material, 4, ethyl 2-bromoacetate, 5, and K2 CO3 in acetone medium. The target compound, pyrido[1,2-a] benzimidazole-2,4-dione, 7, was synthesized by using the last starting material, 5, in sodium ethoxide medium. The compound, 7, can be found in two forms which are keto and enol which would be evaluated in this study. For the evaluation, it was performed some spectroscopic studies. In addition, it was evaluated experimentally obtained acidity constant, pKa value and tautomeric equilibrium of the compound, 7, by using ultraviolet-visible (UV-Vis) spectrophotometer. All of these studies have shown that the valid form of the compound, 7, is keto form.