An electrochemical method for the synthesis of tricyclic heterocycles with high fungicidal activity was developed at the ZIOC.

Recently, the idea of using electric current as an environmentally friendly and cheaper alternative to traditional chemical reagents has been one of the most actively developing areas of modern organic chemistry. Selective electrosynthesis of complex heterocyclic compounds is among the most demanded, but difficult to achieve goals.

An electrochemical method for the synthesis of tricyclic heterocycles — substituted tetrahydroquinolines from basic organic compounds — imines and ethers — was developed at the Laboratory for the Study of Homolytic Reactions of the ZIOC. The electrosynthesis proceeds via the formation of an enol ether from an ether followed by a [4+2] aza-cycloaddition. It is important to note that such a process cannot be carried out using traditional chemical oxidizers.

Together with colleagues from the Mendeleev University and the All-Russian Research Institute of Phytopathology, it was shown that the obtained tetrahydroquinolines have great potential for use as plant protection products, since they have a high fungicidal activity that exceeds the activity of the widely used commercial drug Triadimefon.

Source:

Vera A. Vil’, Sergei S. Grishin, Elena P. Baberkina, Anna L. Alekseenko, Alexey P. Glinushkin, Alexey E. Kovalenko, Alexander O. Terent’ev Electrochemical Synthesis of Tetrahydroquinolines from Imines and Cyclic Ethers via Oxidation/Aza-Diels-Alder Cycloaddition Adv. Synth. Catal. 2022, accepted manuscript. DOI: 10.1002/adsc.202101355.