Synthesis of 6-Alkoxy- and 1,6-Dialkoxy-4-amino-1-aryl-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles

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...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2020-07, Vol.56 (7), p.1187-1190
Main Authors: Kayukov, Ya. S., Grigor’ev, A. A., Karpov, S. V., Kayukova, O. V., Mikhaylov, A. A.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary: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-1 H -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-1 H -pyrrolo[3,4- c ]pyridine-7-carbonitriles.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428020070106