Electrochemical Reduction of 2-Substituted Quinoxalines in Aprotic Medium and in Conditions of Protonation

Tsmokalyuk, Anton; Mozharovskaia, Polina; Belina, Ekaterina; Balin, Ivan; Nosova, Emilia; Matern, Anatoly; Kozitsina, Alisa

doi:10.22034/abec.2023.703900

Electrochemical Reduction of 2-Substituted Quinoxalines in Aprotic Medium and in Conditions of Protonation

Document Type : Original Article

Authors

Anton Tsmokalyuk ¹

Polina Mozharovskaia ¹

Ekaterina Belina ¹

Ivan Balin ¹

Emilia Nosova ¹^{, 2}

Anatoly Matern ¹

Alisa Kozitsina ¹

¹ Institute of Chemical Engineering, Ural Federal University, Mira 28, Yekaterinburg, Russia, 620002

² I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskaya Str., 22, Yekaterinburg, Russia, 620108

10.22034/abec.2023.703900

Abstract

The present work is devoted to the electrochemical reduction study of presumably biologically active 2-substituted quinoxaline derivatives. In this work, two new quinoxaline derivatives are presented. The electrochemical behavior of this compound in an aprotic medium and while its protonating was investigated via a voltammetric method. Using computational methods, the localization of the reduction centres depending on the compound’s structure was determined. The EPR spectra data obtained by electrochemical generation reduction product proved that the studied quinoxaline’s electroconversion occurs with radical anion formation. The linear correlation between the reduction potential of studied compounds and energy of their affinity to the electron was found (R² = 0.933). This confirms the single reduction mechanism of radical nature for the entire series of studied 2-substituted quinoxaline derivatives. Based on that, the electron-accepting ability of these compounds was compared in order to evaluate their possible bioactivity and to select the most perspective ones among them for further research.

Keywords

Quinoxalines

Cyclic voltammetry

EPR spectroscopy

DFT calculations

Electroreduction

Subjects