Skip to main content
Log in

Reactions of Amidoximes with Metal-Activated Nitriles

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

Abstract

Metal-mediated reactions of amidoximes with nitrile ligands are discussed and recent works of the author are considered to allow the reader to better understand the amidoxime reactivity patterns. General routes of activation of amidoxime and nitrile substrates in the studied reactions are considered. Reactions employing amidoximes as HO- and HN-nucleophiles, as well as reactions of amidoximes with nitrile ligands leading to heterocyclic systems are discussed.

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.

Similar content being viewed by others

References

  1. IUPAC Compendium of Chemical Terminology. https://goldbook.iupac.org.

  2. Yang, C.-I., Zhang, Z.-Z., and Lin, S.-B., Coord. Chem. Rev., 2015, vols. 289–290, p. 289.

    Article  Google Scholar 

  3. Kukushkin, V.Yu. and Pombeiro, A.J.L., Coord. Chem. Rev., 1999, vol. 181, p. 147.

    Article  CAS  Google Scholar 

  4. Kukushkin, V.Y., Tudela, D., and Pombeiro, A.J.L., Coord. Chem. Rev., 1996, vol. 156, p. 333.

    Article  CAS  Google Scholar 

  5. Gerasimchuk, N., Eur. J. Inorg. Chem., 2014, no. 27, p. 4518.

    Article  Google Scholar 

  6. Pombeiro, A.J.L. and Kukushkin, V.Y., Comprehensive Coordination Chemistry II, 2004, vol. 1, p. 631.

    CAS  Google Scholar 

  7. Abele, E. and Abele, R., Curr. Org. Synth., 2014, vol. 11, p. 403.

    Article  CAS  Google Scholar 

  8. Walton, J.C., Acc. Chem. Res., 2014, vol. 47, p. 1406.

    Article  CAS  Google Scholar 

  9. Aly, M.M. and Hamza, M.F., J. Dispersion Sci. Technol., 2013, vol. 34, p. 182.

    Article  CAS  Google Scholar 

  10. Seko, N., Tamada, M., Yoshii, F., et al., Nucl. Instrum. Methods Phys. Res. B, 2005, vol. 236, p. 21.

    Article  CAS  Google Scholar 

  11. Tamada, M., Seko, N., and Yoshii, F., Radiat. Phys. Chem., 2004, vol. 71, p. 223.

    Article  CAS  Google Scholar 

  12. Lobanov, P.S. and Dar’in, D.V., Chem. Heterocycl. Compd., 2013, vol. 49, p. 507.

    Article  CAS  Google Scholar 

  13. Fylaktakidou, K.C., Hadjipavlou-Litina, D.J., Litinas, K.E., et al., Curr. Pharm. Des., 2008, vol. 14, p. 1001.

    Article  CAS  Google Scholar 

  14. Clement, B., Drug Metab. Rev., 2002, vol. 34, p. 565.

    Article  CAS  Google Scholar 

  15. Abele, E., Abele, R., and Lukevics, E., Chem. Heterocycl. Compd., 2003, vol. 39, p. 825.

    Article  CAS  Google Scholar 

  16. Abele, E., Abele, R., and Lukevics, E., Chem. Heterocycl. Compd., 2008, vol. 44, p. 769.

    Article  CAS  Google Scholar 

  17. Bolotin, D.S., Bokach, N.A., and Kukushkin, V.Y., Coord. Chem. Rev., 2016, vol. 313, p. 62.

    Article  CAS  Google Scholar 

  18. Pombeiro, A.J.L. and Kukushkin, V.Y., Reactions of Coordinated Nitriles, Comprehensive Coordination Chemistry II, 2004, vol. 1, p. 639.

    CAS  Google Scholar 

  19. Tfouni, E., Ferreira, K.Q., Doro, F.G., et al., Coord. Chem. Rev., 2005, vol. 249, p. 405.

    Article  CAS  Google Scholar 

  20. Hvastijova, M., Kohout, J., and Buchler, J.W., Coord. Chem. Rev., 1998, vol. 175, p. 17.

    Article  CAS  Google Scholar 

  21. Bokach, N.A. and Kukushkin, V.Y., Russ. Chem. Rev., 2005, vol. 74, p. 153.

    Article  CAS  Google Scholar 

  22. Michelin, R.A., Mozzon, M., and Bertani, R., Coord. Chem. Rev., 1996, vol. 147, p. 299.

    Article  CAS  Google Scholar 

  23. Ahmed, T.J., Knapp, S.M.M., and Tyler, D.R., Coord. Chem. Rev., 2011, vol. 255, p. 949.

    Article  CAS  Google Scholar 

  24. Kukushkin, V.Y. and Pombeiro, A.J.L., Chem. Rev., 2002, vol. 102, p. 1771.

    Article  CAS  Google Scholar 

  25. Kabakchi, E.V., Il’in, V.V., Ignatenko, A.V., and Ponomarenko, V.A., Izv. Akad. Nauk. Ser. Khim., 1993, vol. 8, p. 1453.

    Google Scholar 

  26. Lang, C.S., Wong, S.H., Chow, S., et al., Org. Biomol. Chem., 2016, vol. 4, p. 6826.

    Article  Google Scholar 

  27. Hoang, K.L.M. and Liu, X.-W., Nat. Commun., 2014, vol. 5, p. 5051.

    Article  CAS  Google Scholar 

  28. Su, X., Chen, C., Wang, Y., et al., Chem. Commun., 2013, no. 49, p. 6752.

    Article  CAS  Google Scholar 

  29. Abou-Elkhair, R.A.I., Hassan, A.E.A., Boykin, D.W., and Wilson, W.D., Org. Lett., 2016, vol. 18, p. 4714.

    Article  CAS  Google Scholar 

  30. Bolotin, D.S., Burianova, V.K., Novikov, A.S., et al., Organometallics, 2016, vol. 35, p. 3612.

    Article  CAS  Google Scholar 

  31. Bolotin, D.S., Bokach, N.A., Haukka, M., and Kukushkin, V.Y., ChemPlusChem, 2012, vol. 77, p. 31.

    Article  CAS  Google Scholar 

  32. Bolotin, D.S., Bokach, N.A., Haukka, M., and Kukushkin, V.Y., Inorg. Chem., 2012, vol. 51, p. 5950.

    Article  CAS  Google Scholar 

  33. Bolotin, D.S., Kulish, K.I., Bokach, N.A., et al., Inorg. Chem., 2014, vol. 53, p. 10312.

    Article  CAS  Google Scholar 

  34. Bolotin, D.S., Il’in, M.V., Novikov, A.S., et al., New J. Chem., 2017, vol. 41, p. 1940.

    Article  CAS  Google Scholar 

  35. Roca-López, D., Darú, A., Tejero, T., and Merino, P., RSC Adv., 2016, vol. 6, p. 22161.

    Article  Google Scholar 

  36. Liu, W.X., Zhang, C., Zhang, H., et al., J. Am. Chem. Soc., 2017, vol. 139, p. 8678.

    Article  CAS  Google Scholar 

  37. Bolotin, D.S., Demakova, M.Y., Daines, E.A., et al., Russ. J. Gen. Chem., 2017, vol. 87, p. 37.

    Article  CAS  Google Scholar 

  38. Burianova, V.K. and Bolotin, D.S., Russ. J. Gen. Chem., 2015, vol. 85, p. 2721.

    Article  CAS  Google Scholar 

  39. Demakova, M.Y., Bolotin, D.S., Bokach, N.A., et al., ChemPlusChem, 2015, vol. 80, p. 1607.

    Article  CAS  Google Scholar 

  40. Smirnov, A.S., Butukhanova, E.S., Bokach, N.A., et al., Dalton Trans., 2014, vol. 43, p. 15798.

    Article  CAS  Google Scholar 

  41. Kulish, K.I., Novikov, A.S., Tolstoy, P.M., et al., J. Mol. Struct., 2016, vol. 1111, p. 142.

    Article  CAS  Google Scholar 

  42. Bokach, N.A., Kuznetsova, T.V., Simanova, S.A., et al., Inorg. Chem., 2005, vol. 44, p. 5152.

    Article  CAS  Google Scholar 

  43. Gushchin, P.V., Bokach, N.A., Luzyanin, K.V., et al., Inorg. Chem., 2007, vol. 46, p. 1684.

    Article  CAS  Google Scholar 

  44. Bolotin, D.S., Demakova, M.Y., Novikov, A.S., et al., Inorg. Chem., 2015, vol. 54, p. 4039.

    Article  CAS  Google Scholar 

  45. Bolotin, D.S., Bokach, N.A., Kritchenkov, A.S., et al., Inorg. Chem., 2013, vol. 52, p. 6378.

    Article  CAS  Google Scholar 

  46. Xu, H., Ma, S., Xu, Y., et al., Org. Chem., 2015, vol. 80, p. 1789.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to D. S. Bolotin.

Additional information

Original Russian Text © D.S. Bolotin, 2018, published in Koordinatsionnaya Khimiya, 2018, Vol. 44, No. 2, pp. 94–102.

The article was translated by the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bolotin, D.S. Reactions of Amidoximes with Metal-Activated Nitriles. Russ J Coord Chem 44, 243–251 (2018). https://doi.org/10.1134/S1070328418040024

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070328418040024

Keywords

Navigation