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Synthesis of 3-Aminoimidazo[1,2-a]pyridines from α-Aminopyridinyl Amides

Sophie Régnier, William S. Bechara and André B. Charette*

*Centre in Green Chemistry and Catalysis, Department of Chemistry, University of Montreal, P.O. Box 6128, Station Downtown, Montreal, Quebec H3C 3J7, Canada, Email: andre.charetteumontreal.ca

S. Régnier, W. S. Bechara, A. B. Charette, J. Org. Chem., 2016, 81, 10348-10356.

DOI: 10.1021/acs.joc.6b01324 (free Supporting Information)


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Abstract

3-Aminoimidazo[1,2-a]pyridines are rapidly synthesized via a facile and mild cyclodehydration mediated by the activation of N-Boc-protected 2-aminopyridine-containing amides by triflic anhydride in the presence of 2-methoxypyridine followed by a clean deprotection-aromatization sequence in the presence of K2CO3. Various functional groups and substitution patterns were tolerated under the optimized procedure.

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Key Words

imidazo[1,2-a]pyridines


ID: J42-Y2016