title: Directed solid-phase synthesis of trisubstituted imidazo[4,5-c]pyridines and imidazo[4,5-b]pyridines.
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.
authors.affiliation: Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacký University , 17. Listopadu 12, 771 46 Olomouc, Czech Republic.
authors.forename: Barbora
authors.initials: B
authors.lastname: Lemrová
authors.forename: Petra
authors.initials: P
authors.lastname: Smyslová
authors.forename: Igor
authors.initials: I
authors.lastname: Popa
authors.forename: Tomáš
authors.initials: T
authors.lastname: Oždian
authors.forename: Pawel
authors.initials: P
authors.lastname: Zajdel
authors.forename: Miroslav
authors.initials: M
authors.lastname: Soural
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007536:Isomerism; D011725:Pyridines / Q000138:chemical synthesis*; D060327:Solid-Phase Synthesis Techniques; D013329:Structure-Activity Relationship
chemical_list: D000447:Aldehydes; D007093:Imidazoles; D007202:Indicators and Reagents; D011725:Pyridines
keywords: 1-deazapurines; 2,4-dichloronitropyridine; 3-deazapurines; imidazo[4,5-b]pyridines; imidazo[4,5-c]pyridines; solid-phase synthesis