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ACS Comb Sci. 2014 Oct 13;16(10):558-65. doi: 10.1021/co500090t. Epub 2014 Jul 31.

Directed solid-phase synthesis of trisubstituted imidazo[4,5-c]pyridines and imidazo[4,5-b]pyridines.

Author information

1
Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacký University , 17. Listopadu 12, 771 46 Olomouc, Czech Republic.

Abstract

An efficient method is described for the solid-supported synthesis of imidazo[4,5-b]pyridines and imidazo[4,5-c]pyridines from 2,4-dichloro-3-nitropyridine. The key pyridine building block was reacted with polymer-supported amines, followed by replacement of the second chlorine with amines, nitro group reduction, and imidazole ring closure with aldehydes. Depending on the combination of polymer-supported and solution-phase reagents, the strategy allowed for the simple preparation of the target trisubstituted derivatives with variable positioning of the pyridine nitrogen atom. Additionally, after a slight modification of the method, the preparation of strictly isomeric imidazopyridines was possible.

KEYWORDS:

1-deazapurines; 2,4-dichloronitropyridine; 3-deazapurines; imidazo[4,5-b]pyridines; imidazo[4,5-c]pyridines; solid-phase synthesis

PMID:
25046560
DOI:
10.1021/co500090t
[Indexed for MEDLINE]

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