Skip to main content
SpringerLink
Log in

Synthesis of Amides by Nucleophilic Substitution of Hydrogen in 3-Nitropyridine

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

Abstract

3-Nitropyridine reacted with nitrogen-centered carboxylic acid amide anions in anhydrous DMSO in the presence of K3Fe(CN)6 via oxidative nucleophilic substitution of hydrogen to give previously unknown N-(5-nitropyridin-2-yl) carboxamides. The reaction of nitrobenzene with urea anion in DMSO enabled one-pot synthesis of bis(4-nitrophenyl)amine.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Chupakhin, O.N. and Charushin, V.N., Tetrahedron Lett., 2016, vol. 57, p. 2665.

    Article  CAS  Google Scholar 

  2. Charushin, V.N. and Chupakhin, O.N., Top. Heterocycl. Chem., 2014, vol. 37, p. 1.

    Google Scholar 

  3. Gulevskaya, A.V. and Pozharskii, A.F., Top. Heterocycl. Chem., 2014, vol. 37, p. 179.

    Google Scholar 

  4. Makosza, M. and Wojciechowski, K., Top. Heterocycl. Chem., 2014, vol. 37, p. 51.

    Google Scholar 

  5. Patriciu, O.-I., Finaru, A.-L., Sandulescu, I., and Guillaumet, G., Synthesis, 2007, p. 3868.

    Google Scholar 

  6. Bashkin, J.K., Rains, R., and Stern, M., Green Chem., 1999, vol. 1, p. G41.

    Article  Google Scholar 

  7. Constable, D.J.C., Dunn, P.J., Hayler, J.D., Humphrey, G.R., Leazer, J.L., Linderman, R.J., Lorenz, K., Manley, J., Pearlman, B.A., Wells, A., Zaks, A., and Zhang, T.Y., Green Chem., 2007, vol. 9, p. 411.

    Article  CAS  Google Scholar 

  8. Utepova, I.A., Trestsova, M.A., Chupakhin, O.N., Charushin, V.N., and Rempel, A.A., Green Chem., 2015, vol. 17, p. 4401.

    Article  CAS  Google Scholar 

  9. Wozniak, M., Baranski, A., and Szpakiewicz, B., Justus Liebigs Ann. Chem., 1991, p. 875.

    Google Scholar 

  10. Bakke, J.M. and Svensen, H., Tetrahedron Lett., 2001, vol. 42, p. 4393.

    Article  CAS  Google Scholar 

  11. Bakke, J.M., J. Heterocycl. Chem., 2005, vol. 42, p. 463.

    Article  CAS  Google Scholar 

  12. Szpakiewicz, B. and Wozniak, M., J. Prakt. Chem., 1999, vol. 341, p. 75.

    Article  CAS  Google Scholar 

  13. Gulevskaya, A.V., Maes, B.U.W., Meyers, C., Herrebout, W., and van der Veken, B.J., Eur. J. Org. Chem., 2006, no. 23, p. 5305.

    Article  CAS  Google Scholar 

  14. Verbeeck, S., Herrebout, W.A., Gulevskaya, A.V., van der Veken, B.J., and Maes, B.U.W., J. Org. Chem., 2010, vol. 75, p. 5126.

    Article  CAS  PubMed  Google Scholar 

  15. Bakke, J.M., Svensen, H., and Trevisan, R., J. Chem. Soc., Perkin Trans. 1, 2001, p. 376.

    Google Scholar 

  16. Seko, S. and Miyake, K., Chem. Commun., 1998, no. 15, p. 1519.

    Article  Google Scholar 

  17. Makosza, M. and Bialecki, M., J. Org. Chem., 1998, vol. 63, p. 4878.

    Article  CAS  Google Scholar 

  18. Holt, J., Tjosås, F., Bakke, J.M., and Fiksdahl, A., J. Heterocycl. Chem., 2004, vol. 41, p. 987.

    Article  CAS  Google Scholar 

  19. Stern, M.K. and Cheng, B.K., J. Org. Chem., 1993, vol. 58, p. 6883.

    Article  CAS  Google Scholar 

  20. Gulevskaya, A.V., Tyaglivaya, I.N., Verbeeck, S., Maes, U.W., and Tkachuk, A.V., Arkivoc, 2011, part (ix), p. 238.

    Google Scholar 

  21. Borovlev, I.V., Demidov, O.P., Kurnosova, N.A., Amangasieva, G.A., and Avakyan, E.K., Chem. Heterocycl. Compd., 2015, vol. 51, p. 170.

    Article  CAS  Google Scholar 

  22. Borovlev, I.V., Demidov, O.P., Amangasieva, G.A., Avakyan, E.K., and Kurnosova, N.A., Arkivoc, 2016, part (iii), p. 58.

    Google Scholar 

  23. Demidov, O.P., Borovlev, I.V., Amangasieva, G.A., and Avakyan, E.K., Chem. Heterocycl. Compd., 2016, vol. 52, p. 104.

    Article  CAS  Google Scholar 

  24. Borovlev, I.V., Demidov, O.P., Amangasieva, G.A., and Avakyan, E.K., Tetrahedron Lett., 2016, vol. 57, p. 3608.

    Article  CAS  Google Scholar 

  25. Demidov, O.P., Borovlev, I.V., Saigakova, N.A., Nemykina, O.A., Demidova, N.V., and Pisarenko, S.V., Chem. Heterocycl. Compd., 2011, vol. 47, p. 114.

    Article  CAS  Google Scholar 

  26. Demidov, O.P., Borovlev, I.V., Pisarenko, S.V., Nemykina, O.A., and Saigakova, N.A., Chem. Heterocycl. Compd., 2010, vol. 46, p. 636.

    Article  CAS  Google Scholar 

  27. Borovlev, I.V., Demidov, O.P., and Saigakova, N.A., Russ. Chem. Bull., Int. Ed., 2011, vol. 60, p. 1784.

    Article  CAS  Google Scholar 

  28. Borovlev, I.V., Demidov, O.P., Saigakova, N.A., Pisarenko, S.V., and Nemykina, O.A., J. Heterocycl. Chem., 2011, vol. 48, p. 1206.

    Article  CAS  Google Scholar 

  29. Finch, N., Campbell, T.R., Gemenden, C.W., and Povalski, H.J., J. Med. Chem., 1980, vol. 23, p. 1405.

    Article  CAS  PubMed  Google Scholar 

  30. Amangasieva, G.A., Borovlev, I.V., Demidov, O.P., Kurnosova, N.A., and Avakyan, E.K., Chem. Heterocycl. Compd., 2015, vol. 51, p. 586.

    Article  CAS  Google Scholar 

  31. Borovlev, I.V., Demidov, O.P., Amangasieva, G.A., Avakyan, E.K., and Kurnosova, N.A., J. Heterocycl. Chem., 2017, vol. 54, p. 406.

    Article  CAS  Google Scholar 

  32. Pozharskii, A.F. and Konstantinchenko, A.A., Chem. Heterocycl. Compd., 1972, vol. 8, p. 1518.

    Article  Google Scholar 

  33. Kitahara, T., Ishihara, Y., and Takano, J., Nippon Kagaku Zasshi, 1997, vol. 12, p. 876; Chem. Abstr., 1997, vol. 128, no. 22 802.

    Article  Google Scholar 

  34. Gottlieb, H.E., Kotlyar, V., and Nudelman, A., J. Org. Chem., 1997, vol. 62, p. 7512.

    Article  CAS  Google Scholar 

  35. Kokars, V., Yanishevskii, A., and Kampars, V., Chem. Heterocycl. Compd., 2002, vol. 38, p. 805.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. North Caucasus Federal University, ul. Pushkina 1a, Stavropol, 355009, Russia

    G. A. Amangasieva, I. V. Borovlev, O. P. Demidov, E. K. Avakyan & A. A. Borovleva

Authors
  1. G. A. Amangasieva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. V. Borovlev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. P. Demidov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. K. Avakyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. A. Borovleva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. V. Borovlev.

Additional information

Original Russian Text © G.A. Amangasieva, I.V. Borovlev, O.P. Demidov, E.K. Avakyan, A.A. Borovleva, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 6, pp. 865–870.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Amangasieva, G.A., Borovlev, I.V., Demidov, O.P. et al. Synthesis of Amides by Nucleophilic Substitution of Hydrogen in 3-Nitropyridine. Russ J Org Chem 54, 867–872 (2018). https://doi.org/10.1134/S1070428018060076

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428018060076

Search

Navigation