Researchers of the Zelinsky Institute proposed an electrochemical method for the synthesis of imidazoles

Imidazoles are the basic class of heterocyclic compounds, widely represented in the structures of natural compounds, pharmaceuticals, and functional materials. Researchers from the Laboratory of Homolytic Reactions of the ZIOC ​​proposed an electrochemical method for the synthesis of imidazoles from vinyl azides and benzylamines.

The use of electric current allows the reaction to be carried out without the use of non-recyclable chemical oxidants. The process was carried out under direct current conditions in an experimentally simple undivided electrochemical cell with a platinum cathode and a glassy carbon anode. Using cyclic voltammetry and control experiments, a possible reaction route was proposed. Presumably, during the reaction, 2H-azirine is formed from vinyl azide, which then reacts with benzylamine and the corresponding imine. Cyclization and aromatization of the resulting intermediate lead to the desired imidazole.

Source:

Vera A. Vil’, Sergei S. Grishin, Alexander O. Terent’ev Electrochemically Induced Synthesis of Imidazoles from Vinyl Azides and Benzyl Amines // Molecules 2022, 27, 7721. DOI: 10.3390/molecules27227721.