Synthesis and Study of Prototropic Tautomerism of 2-(2-Furyl)-1-hydroxyimidazoles

Abstract

Novel 2-(2-furyl)imidazole derivatives were synthesised. 2-(2-Furyl)-1-methoxyimidazoles and 2-(2-furyl)-1-methylimidazole 3-oxides were used as model compounds in the study of the prototropic tautomerism of 2-(2-furyl)-1-hydroxyimidazoles by means of 1H, 13C NMR and UV/vis spectroscopies. It was demonstrated that the interaction of the π-excessive furyl moiety with an electron-withdrawing carbonyl group in position 5 of imidazole stabilised the N-hydroxy tautomeric form in both deuterated chloroform and d6-DMSO. In ethanol the N-oxide tautomer is also present along with the prevailing N-hydroxyimidazole.