Electrochemical CH alkylation of N-heterocycles via aromatization-driven CC fragmentation of unstrained ketones

Abstract

Herein, we report an electrochemically driven direct CH alkylation of N-heterocycles using readily accessible pro-aromatic dihydroquinazolinones derived from simple ketones as alkylating reagents. This protocol employs an operationally simple undivided cell and inexpensive materials, reticulated vitreous carbon (RVC) and magnesium, as the electrodes. Notably, this practical electrochemical approach proceeds under chemical oxidant-free conditions, and a vast array of valuable alkylated N-heterocycles (more than 40 examples), including quinoxalin-2(1H)-ones, azauracils, pyrazinones, quinoxalines, quinazolines, quinolines, and phenanthridines, can be readily constructed at room temperature.