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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REFERENCES
Grigor’ev, A.A., Kayukov, Ya.S., Nikiforova, A.L., Karpov, S.V., Shchegravina, E.S., Kayukova, O.V., and Tafeenko, V.A., Chem. Heterocycl. Compd., 2019, vol. 55, p. 167. https://doi.org/10.1007/s10593-019-02434-4
Kayukov, Ya.S., Karpov, S.V., Grigor’ev, A.A., Nikiforova, A.L., Nasakin, O.E., Shchegravina, E.S., Kayukova, O.V., and Tafeenko, V.A., Chem. Heterocycl. Compd., 2017, vol. 53, p. 568. https://doi.org/10.1007/s10593-017-2093-x
Lam, B., Arikawa, Y., Cramlett, J., Dong, Q., de Jong, R., Feher, V., Grimshaw, C.E., Farrell, P.J., Hoffman, I.D., Jennings, A., Jones, B., Matuszkiewicz, J., Miura, J., Miyake, H., Natala, S.R., Shi, L., Takahashi, M., Taylor, E., Wyrick, C., Yano, J., Zalevsky, J., and Nie, Z., Bioorg. Med. Chem. Lett., 2016, vol. 26, p. 5947. https://doi.org/10.1016/j.bmcl.2016.10.087
Grigoreva, T.A., Novikova, D.S., Petukhov, A.V., Gureev, M.A., Garabadzhiu, A.V., Melino, G., Barlev, N.A., and Tribulovich, V.G., Bioorg. Med. Chem. Lett., 2017, vol. 27, p. 5197. https://doi.org/10.1016/j.bmcl.2017.10.049
Deraeve, C., Dorobantu, I.M., Rebbah, F., Le Quéméner, F., Constant, P., Quémard, A., Bernardes-Génisson, V., Bernadou, J., and Pratviel, G., Bioorg. Med. Chem., 2011, vol. 19, p. 6225. https://doi.org/10.1016/j.bmc.2011.09.017
Kayukov, Ya.S., Bardasov, I.N., Karpov, S.V., Ershov, O.V., Nasakin, O.E., Kayukova, O.V., and Tafeenko, V.A., Russ. J. Org. Chem., 2012, vol. 48, p. 1447. https://doi.org/10.1134/S1070428012110073
ACKNOWLEDGMENTS
A part of this work was performed in the framework of state assignment for Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, in the field of basic research.
Funding
This study was performed under financial support by the Russian Foundation for Basic Research (project no. 18-33-01204_mol_a).
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Kayukov, Y.S., Grigor’ev, A.A., Karpov, S.V. et al. 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. Russ J Org Chem 56, 1187–1190 (2020). https://doi.org/10.1134/S1070428020070106
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DOI: https://doi.org/10.1134/S1070428020070106