Iron(III)-Catalyzed Cascade Reaction between Nitroolefins and 2-Aminopyridines: Synthesis of Imidazo[1,2-a]pyridines and Easy Access towards Zolimidine

• Published in: Advanced synthesis & catalysis Vol. 355; no. 6; pp. 1065 - 1070
• Main Authors: Santra, Sougata, Bagdi, Avik Kumar, Majee, Adinath, Hajra, Alakananda
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 15.04.2013; WILEY‐VCH Verlag; Wiley
• Subjects: 2-a]pyridines; cascade reactions; Cascades; Catalysis; Chemistry; Chemistry, Applied; Chemistry, Organic; Denitration; Drugs; imidazo; imidazo[1,2‐a]pyridines; iron(III) chloride; Methodology; nitroolefins; Peptic ulcers; Physical Sciences; Pyridines; Science & Technology; Synthesis; zolimidine; DIRECT ARYLATION; 3-COMPONENT COUPLING REACTION; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; BAYLIS-HILLMAN ACETATES; 2-a]pyridines; iron(III) chloride; cascade reactions; MULTICOMPONENT REACTIONS; ANTITUMOR EVALUATION; imidazo; nitroolefins; zolimidine; NANO INDIUM OXIDE; DERIVATIVES; C-H
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201201112

The iron(III)‐catalyzed one‐pot cascade reaction between nitroolefins and 2‐aminopyridines has been demonstrated for the synthesis of imidazo[1,2‐a]pyridines by exploiting the bielectrophilic nature of nitroolefins. This methodology could be successfully applicable for the synthesis of zolimidine, a useful drug for the treatment of peptic ulcer. The reaction proceeds through Michael addition followed by intramolecular cyclization and in situ denitration.