Abstract
A potential of using nickel complexes with 1,3-dicarbonyl compounds for the transformation of heterocyclic aminonitriles into fused systems with a 4-aminopyridine core was evaluated. A possibility of introducing acidophobic groups into the molecules of fused compounds was shown.
Similar content being viewed by others
REFERENCES
Schneller, S.W. and Luo, J.-K., J. Org. Chem., 1980, vol. 45, no. 20, p. 4045. https://doi.org/10.1021/jo01308a021
Klemm, L.H., Louris, J.N., Boisvert, W., Higgins, C., and Muchiri, D.R., J. Heterocycl. Chem., 1985, vol. 22, no. 5, p. 1249. https://doi.org/10.1002/jhet.5570220522
Klemm, L.H., Wang, J., and Sur, S.K., J. Heterocycl. Chem., 1990, vol. 27, no. 6, p. 1537. https://doi.org/10.1002/jhet.557027063
Meade, E.A. and Beauchamp, L.M., J. Heterocycl. Chem., 1996, vol. 33, no. 2, p. 303. https://doi.org/10.1002/jhet.5570330215
Hohn, H., Denzel, Th., and Janssen, W., J. Heterocycl. Chem., 1972, vol. 9, p. 235. https://doi.org/10.1002/jhet.5570090212
Bare, T.M., McLaren, C.D., Campbell, J.B., Firor, J.W., Resch, J.F., Walters, C.P., Salama, A.I., Meiners, B.A., and Patel, J.B., J. Med. Chem., 1989, vol. 32, no. 12, p. 2561. https://doi.org/10.1021/jm00132a011
Hulpia, F., Noppen, S., Schols, D., Andrei, G., Snoeck, R., Liekens, S., Vervaeke, P., and Van Calenbergh, S., Eur. J. Med. Chem., 2018, vol. 157, p. 248. https://doi.org/10.1016/j.eimech.2018.07.062
Kendre, D.B., Toche, R.B., and Jachak, M.N., Tetrahedron, 2007, vol. 63, no. 45, p. 11000. https://doi.org/10.1016/j.tet.2007.08.052
Russell, R.K. and Lever, W.O., Synth. Commun., 1993, vol. 23, no. 20, p. 2931. https://doi.org/10.1080/00397919308012615
Rochling, H. and Buchel, K.H., Chem. Ber., 1971, vol. 104, no. 1, p. 344. https://doi.org/10.1002/cber.19711040140
Mascal, M., Hext, N.M., Warmuth, R., Arnall-Culiford, J.R., Moore, M.H., and Turkenburg, J.R., J. Org. Chem., 1999, vol. 64, no. 23, p. 8479. https://doi.org/10.1021/jo990719t
Komarova, E.S., Makarov, V.A., Alekseeva, L.M., Avramenko, G.V., and Granik, V.G., Russ. Chem. Bull., 2007, vol. 56, no. 11, p. 2337. https://doi.org/10.1007/s11172-007-0369-5
Silva, D., Chioua, M., Samadi, A., Carmo, C., Jimero, M.-L., Mendes, E., Rios, C., Romero, A., Villarroya, M., Lopez, M., and Marco-Contelles, J., Eur. J. Med. Chem., 2011, vol. 46, no. 9, p. 4676. https://doi.org/10.1016/j.ejmech.2011.05.068
Corre, L., Tak-Tak, L., Guillard, A., Prestat, G., GravierDelletier, C., and Busca, D., Org. Biomol. Chem., 2015, vol. 13, no. 2, p. 409. https://doi.org/10.1039/C4OB01951B
Rodrigues, L.M., Francisco, C.S., Oliveira-Campos, A.M., and Salaheldin, A.M., Synth. Commun., 2008, vol. 38, no. 24, p. 4369. https://doi.org/10.1080/00397910802331638
Thomae, D., Perspicate, E., Hesse, S., Kirsch, G., and Seck, P., Tetrahedron, 2008, vol. 64, no. 39, p. 9309. https://doi.org/10.1016/j.tet.2008.07.017
Hu, H., Song, L., Fang, Q., Zheng, J., Meng, Z., and Luo, Y., Molecules, 2011, vol. 16, no. 2, p. 1878. https://doi.org/10.3390/molecules16021878
Potapov, A.Yu., Vandyshev, D.Yu., Kosheleva, Y.A., Polikarchuk, V.A., Potapov, M.A., and Shikhaliev, V.S., Chem. Heterocycl. Compd., 2017, vol. 53, no. 2, p. 207. https://doi.org/10.1007/s10593-017-2041-9
Frasson, I., Spano, V., Di Martino, S., Nadai, M., Doria, F., Parrino, B., Carbone, A., Cascioferro, S.M., Diana, P., Cirrincione, G., Freccero, M., Barraja, P., Richter, S.N., and Montalbano, A., Eur. J. Med. Chem., 2018, vol. 162, p. 176. https://doi.org/10.1016/j.ejmech.2018.10.071
Forbes, I.T., Johnson, G.N., and Thompson, M., J. Chem. Soc. Perkin Trans. 1, 1992, no. 2, p. 275. https://doi.org/10.1039/P19920000275
Thomae, D., Kirch, G., and Seck, P., Synthesis, 2007, no. 7, p. 1027. https://doi.org/10.1055/s-2007-965944
Lalezari, I., J. Heterocycl. Chem., 1979, vol. 16, no. 3, p. 603. https://doi.org/10.1002/jhet.5570160341
Song, Y.-H. and Seo, J., J. Heterocycl. Chem., 2007, vol. 44, no. 12, p. 1439. https://doi.org/10.1002/jhet.5570440631
Vasil’ev, L.S., Sheremetev, A.V., Khoa, N.K., Dem’yanets, Z.K., Dmitriev, D.E., and Dorokhov, V.A., Russ. Chem. Bull., 2001, vol. 50, no. 7, p. 1280. https://doi.org/10.1023/A:1014075327382
Corain, B., Basato, M., Ballota, C., and Ahmed, M., Inorg. Chim. Acta, 1984, vol. 87, no. 1, p. 105. https://doi.org/10.1016/S0020-1693(00)83629-4
Nelson, J.H., Howells, P.N., DeLullo, G.C., Landen, G.L., and Henry, R.A., J. Org. Chem., 1980, vol. 45, no. 7, p. 1246. https://doi.org/10.1021/jo01295a017
Yarovenko, V.N., Krayushkin, M.M., Lysenko, O.V., Kustov, L.M., and Zavarzin, I.V., Russ. Chem. Bull., 1994, vol. 43, no. 3, p. 402. https://doi.org/10.1007/BF01169715
Cabbe, G., Gadts, F., and Toppet, S., Bull. Soc. Chim. Belg., 1985, vol. 94, no. 7, p. 441. https://doi.org/10.1002/bscb.19850940702
Cheng, C.C. and Robins, R.K., J. Org. Chem., 1956, vol. 21, no. 11, p. 1240. https://doi.org/10.1021/jo01117a010
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
No conflict of interest was declared by the authors.
Rights and permissions
About this article
Cite this article
Vydzhak, R.N., Panchishin, S.Y. & Brovarets, V.S. Application of Nickel Complexes with 1,3-Dicarbonyl Compounds for Synthesis of Fused 4-Aminopyridine-Based Systems. Russ J Gen Chem 90, 1439–1446 (2020). https://doi.org/10.1134/S1070363220080101
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363220080101