Electro- and Mechanochemical Strategy as a Dual Synthetic Approach for Biologically Relevant 3-Nitro-imidazo-[1,2- a]pyridines

J Org Chem. 2024 Sep 6;89(17):12071-12084. doi: 10.1021/acs.joc.4c00881. Epub 2024 Aug 15.

Abstract

We herein disclose a dual synthetic approach involving electrochemical and mechanochemical strategies for diversely functionalized 3-nitro-2-aryl-immidazo[1,2-a]pyridines. Both methods offer a practical and straightforward alternative route for accessing this important class of biologically promising nitrogen-containing heterocycles. Significant advantages of the newly developed methods include mild and energy-efficient reaction conditions, avoidance of transition metal catalysts, external heating and additional oxidants, shorter reaction times, good to excellent yields, broad substrate scope, gram-scale applicability, operational simplicity, and eco-friendliness. Furthermore, a synthetic application was extended by successfully reducing synthesized 3-nitro-2-aryl-immidazo[1,2-a]pyridines to their corresponding amino derivatives.