Exploration of versatile reactions on 2-chloro-3-nitroimidazo[1,2-a] pyridine: Expanding structural diversity of C2- and C3-functionalized imidazo[1,2-a]pyridines

Article abstract of DOI:10.1016/j.tetlet.2013.07.113

Alternative strategies for functionalizing 2-chloro-3-nitroimidazo[1,2-a] pyridine have been developed. Suzuki-Miyaura cross-coupling reaction provided easily the corresponding 2-arylated compounds, and herefrom the nitro group was reduced into amine which afforded amides, anilines, and ureas in the 3-position. The amination of the key compound using a metal-catalyzed reaction was reported. This study highlighted the importance of the nitro group to facilitate the chlorine displacement. Other nucleophilic aromatic substitutions open a route to various products derived from imidazo[1,2-a]pyridine.