Skip to main content
Log in

Application of Nickel Complexes with 1,3-Dicarbonyl Compounds for Synthesis of Fused 4-Aminopyridine-Based Systems

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Schneller, S.W. and Luo, J.-K., J. Org. Chem., 1980, vol. 45, no. 20, p. 4045. https://doi.org/10.1021/jo01308a021

    Article  CAS  Google Scholar 

  2. 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

    Article  CAS  Google Scholar 

  3. 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

    Article  CAS  Google Scholar 

  4. Meade, E.A. and Beauchamp, L.M., J. Heterocycl. Chem., 1996, vol. 33, no. 2, p. 303. https://doi.org/10.1002/jhet.5570330215

    Article  CAS  Google Scholar 

  5. Hohn, H., Denzel, Th., and Janssen, W., J. Heterocycl. Chem., 1972, vol. 9, p. 235. https://doi.org/10.1002/jhet.5570090212

    Article  Google Scholar 

  6. 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

    Article  CAS  PubMed  Google Scholar 

  7. 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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. 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

    Article  CAS  Google Scholar 

  9. Russell, R.K. and Lever, W.O., Synth. Commun., 1993, vol. 23, no. 20, p. 2931. https://doi.org/10.1080/00397919308012615

    Article  CAS  Google Scholar 

  10. Rochling, H. and Buchel, K.H., Chem. Ber., 1971, vol. 104, no. 1, p. 344. https://doi.org/10.1002/cber.19711040140

    Article  Google Scholar 

  11. 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

    Article  CAS  Google Scholar 

  12. 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

    Article  CAS  Google Scholar 

  13. 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

    Article  CAS  PubMed  Google Scholar 

  14. 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

    Article  PubMed  Google Scholar 

  15. 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

    Article  CAS  Google Scholar 

  16. 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

    Article  CAS  Google Scholar 

  17. 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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. 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

    Article  CAS  Google Scholar 

  19. 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

    Article  CAS  PubMed  Google Scholar 

  20. 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

    Article  Google Scholar 

  21. Thomae, D., Kirch, G., and Seck, P., Synthesis, 2007, no. 7, p. 1027. https://doi.org/10.1055/s-2007-965944

    Article  CAS  Google Scholar 

  22. Lalezari, I., J. Heterocycl. Chem., 1979, vol. 16, no. 3, p. 603. https://doi.org/10.1002/jhet.5570160341

    Article  CAS  Google Scholar 

  23. Song, Y.-H. and Seo, J., J. Heterocycl. Chem., 2007, vol. 44, no. 12, p. 1439. https://doi.org/10.1002/jhet.5570440631

    Article  CAS  Google Scholar 

  24. 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

    Article  Google Scholar 

  25. 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

    Article  CAS  Google Scholar 

  26. 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

    Article  CAS  Google Scholar 

  27. 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

    Article  Google Scholar 

  28. 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

    Article  Google Scholar 

  29. Cheng, C.C. and Robins, R.K., J. Org. Chem., 1956, vol. 21, no. 11, p. 1240. https://doi.org/10.1021/jo01117a010

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. S. Brovarets.

Ethics declarations

No conflict of interest was declared by the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

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

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363220080101

Keywords:

Navigation