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Novel one step synthesis of imidazo[1,2-a]pyridines and Zolimidine via iron/iodine-catalyzed Ortoleva-King type protocol
Institution:1. School of Chemical Sciences, Mahatma Gandhi University, Priyadarsini Hills P O, Kottayam, Kerala 686560, India;2. Advanced Molecular Materials Research Centre (AMMRC) Mahatma Gandhi University, Priyadarsini Hills P O, Kottayam, Kerala 686 560, India;1. Department of Organic Chemistry, Saint-Petersburg State Institute of Technology, Saint Petersburg 190013, Russia;2. Department of Natural Compounds Chemistry, Institute of Chemistry, Saint-Petersburg State University, Saint Petersburg 198504, Russia
Abstract:Imidazo1,2-a]pyridines form versatile scaffolds in pharmaceutical industry arising from their diverse biological activities. The synthesis of these molecules thus has been of great interest and resulted in the development of a large number of new methodologies. Herein we describe the first iron-catalyzed Ortoleva-King type protocol towards the synthesis of these fused heterocyclic compounds. This methodology employs cheap and easily available FeCl3·6H2O and molecular iodine as the catalytic system. The procedure has been well explored by extending the substrate scope with a variety of aromatic ketones and 2-aminopyridines to furnish different imidazo1,2-a]pyridine derivatives in moderate to good yields. A successful application of this protocol was also demonstrated by achieving direct one step synthesis of the gastro protective drug, Zolimidine.
Keywords:Ortoleva-King reaction  Iron  Iodine
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