Abstract
Base-catalyzed reaction of 3-aroyl-6-halopyridine-3,5-dicarbonitriles with alcohols involved successive regioselective pyrrole ring fusion at the pyridine [c] side and nucleophilic substitution of chlorine. Pyrrole ring closure is the result of initial formation of furan ring with participation of the carbonyl and cyano groups, followed by iminolactone–lactam rearrangement. The reaction in anhydrous alcohol afforded 1,6-dialkoxy-4-amino-1-aryl-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles. If water was present in the alcohols, the products were 6-alkoxy-4-amino-1-aryl-1-hydroxy-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles.
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