Synthesis of alkoxy-substituted Pyridines from mono- and tricationic pyridinium salts

Nucleophilic substitution reactions on 4-(4-dimethylamino)-pyridinium-substituted tetrachloropyridine with oxygen nucleophiles such as alkoxides and phenolates resulted in the formation of 4- or 2,4-alkoxy- or -phenoxy-substituted chloropyridines depending on the reaction conditions. Substitution on 2,4,6-tris(4-dimethylamino)pyridinium-substituted 3,5-dichloropyridine gave the corresponding 2,4,6-tris-alkoxy- or -phenoxy-substituted pyridines which are not available by other routes.