Synthesis and Study of Prototropic Tautomerism of 2-(2-Furyl)-1-hydroxyimidazoles
Polina A. Nikitina
A B C , Tatiana Yu. Koldaeva A , Marina A. Zakharko B and Valery P. Perevalov A
A Department of Fine Organic Synthesis and Chemistry of Dyes, D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya Square, 9, Moscow, 125047, Russia.
B A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Street, 28, Moscow, 119991, Russia.
C Corresponding author. Email: polinandrevna@yandex.ru
Australian Journal of Chemistry 73(11) 1098-1104 https://doi.org/10.1071/CH20044
Submitted: 10 February 2020 Accepted: 26 March 2020 Published: 4 June 2020
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.
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