Copper-Catalyzed Synthesis of Imidazo[1,2-a]pyridines through Tandem Imine Formation-Oxidative Cyclization under Ambient Air: One-Step Synthesis of Zolimidine on a Gram-Scale

• Published in: Advanced synthesis & catalysis Vol. 355; no. 9; pp. 1741 - 1747
• Main Authors: Bagdi, Avik Kumar, Rahman, Matiur, Santra, Sougata, Majee, Adinath, Hajra, Alakananda
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 17.06.2013; WILEY‐VCH Verlag; Wiley
• Subjects: 2-a]pyridines; ambient air; Aromatic compounds; Catalysis; Chemistry; Chemistry, Applied; Chemistry, Organic; copper; cyclization; Drugs; Functional groups; imidazo; imidazo[1,2‐a]pyridines; Imines; Ketones; oxidative amination; Physical Sciences; Science & Technology; Synthesis; zolimidine; ROUTE; DIRECT ARYLATION; ONE-POT SYNTHESIS; 2-a]pyridines; BETA-KETO-ESTERS; cyclization; BROMIDES; FUNCTIONALIZATION; 2-AMINOPYRIDINES; imidazo; ambient air; oxidative amination; DIAMINATION; copper; zolimidine; N BOND FORMATION; C-H AMINATION
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201300298

A new copper‐catalyzed oxidative cyclization via CH amination between 2‐aminopyridines and methyl aryl/heteroaryl ketones has been developed under ambient air. Imidazo[1,2‐a]pyridines containing a wide range of functional groups have been synthesized from basic and easily available starting materials. This simple, one‐pot reaction protocol is applicable for the direct preparation of zolimidine (a marketed antiulcer drug) on a large scale.