Solvent and catalyst‐free synthesis of imidazo[1,2‐a]pyridines by grindstone chemistry

• Published in: Journal of heterocyclic chemistry 2021-01, Vol.58 (1), p.250-259
• Main Authors: Godugu, Kumar, Nallagondu, Chinna Gangi Reddy
• Format: Article
• Language: English
• ISSN: 0022-152X; 1943-5193
• DOI: 10.1002/jhet.4164

The present work describes the solvent and catalyst‐free synthesis of imidazo[1,2‐a]pyridines in excellent to nearly quantitative yields from 2‐aminopyridines and a wide variety of ω‐bromomethylketones using a grindstone procedure at 25°C to 30°C for 3 to 5 minutes. The absolute structure of the compound, 2‐(3‐bromophenyl)‐7‐methylimidazo[1,2‐a]pyridine is determined by X‐ray crystallography. This green strategy has several noteworthy advantages such as wide spread substrate scope, short reaction times, water work up and the products do not require any chromatographic purification. Moreover, the method does not require any specialized equipment and is highly economical, environmentally benign and easy to carry out in any laboratory. Hence, the developed method meets the concept of “benign by design” and is greener alternative to the reported procedures for the synthesis of imidazo[1,2‐a]pyridines.