Directed solid-phase synthesis of trisubstituted imidazo[4,5-c]pyridines and imidazo[4,5-b]pyridines
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
25046560
DOI
10.1021/co500090t
Knihovny.cz E-resources
- Keywords
- 1-deazapurines, 2,4-dichloronitropyridine, 3-deazapurines, imidazo[4,5-b]pyridines, imidazo[4,5-c]pyridines, solid-phase synthesis,
- MeSH
- Aldehydes chemistry MeSH
- Imidazoles chemical synthesis MeSH
- Indicators and Reagents MeSH
- Isomerism MeSH
- Pyridines chemical synthesis MeSH
- Solid-Phase Synthesis Techniques * MeSH
- Structure-Activity Relationship MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Aldehydes MeSH
- Imidazoles MeSH
- Indicators and Reagents MeSH
- Pyridines MeSH
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.
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