On the mechanism of the direct acid catalyzed formation of 2,3-disubstituted imidazo[1,2-a]pyridines from 2-aminopyridines and acetophenones. Concurrence between ketimine and Ortoleva–King type reaction intermediated transformations??

RSC Advances Pub Date: 2013-10-31 DOI: 10.1039/C3RA45005H

Abstract

Direct acid catalyzed formation of 2,3-disubstituted imidazo[1,2-a]pyridines from 2-aminopyridines and acetophenones was studied in order to gain insight into the reaction mechanism. The formation of differently substituted products was explained by a concurrent ketimine and Ortoleva–King type reaction intermediated transformations. The dependence of the reaction output on the catalyst used and on acetophenone and pyridine substituents was discussed.

Graphical abstract: On the mechanism of the direct acid catalyzed formation of 2,3-disubstituted imidazo[1,2-a]pyridines from 2-aminopyridines and acetophenones. Concurrence between ketimine and Ortoleva–King type reaction intermediated transformations
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