Skip to main content
SpringerLink
Log in

Synthesis of 4-Acyl-2-amino-6-(arylsulfanyl)pyridine-3,5-dicarbonitriles

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

Abstract

The reaction of 4-acyl-2-amino-6-chloropyridine-3,5-dicarbonitriles with aromatic thiols in 1,4-dioxane in the presence of triethylamine led to the formation of 4-acyl-2-amino-6-(arylsulfanyl)pyridine-3,5-dicarbonitriles.

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.

Scheme
Scheme

REFERENCES

  1. Kanani, M.B. and Patel, M.P., Med. Chem. Res., 2013, vol. 22, p. 2912. https://doi.org/10.1007/s00044-012-0292-7

    Article  CAS  Google Scholar 

  2. Makawana, J.A., Patel, M.P., and Patel, R.G., Med. Chem. Res., 2012, vol. 21, p. 616. https://doi.org/10.1007/s00044-011-9568-6

    Article  CAS  Google Scholar 

  3. Grigor’ev, A.A., Shtyrlin, N.V., Gabbasova, R.R., Zeldi, M.I., Grishaev, D.Yu., Gnezdilov, O.I., Balakin, K.V., Nasakin, O.E., and Shtyrlin, Y.G., Synth. Commun., 2018, vol. 48, p. 2288. https://doi.org/10.1080/00397911.2018.1501487

    Article  CAS  Google Scholar 

  4. Abbas, H.-A.S., El Sayed, W.A., and Fathy, N.M., Eur. J. Med. Chem., 2010, vol. 45, p. 973. https://doi.org/10.1016/j.ejmech.2009.11.039

    Article  CAS  PubMed  Google Scholar 

  5. Quintela, J.M., Peinador, C., Veiga, M.C., Botana, L.M., Alfonso, A., and Riguera, R., Eur. J. Med. Chem., 1998, vol. 33, p. 887. https://doi.org/10.1016/S0223-5234(99)80013-0

    Article  CAS  Google Scholar 

  6. Attaby, F.A., Elghandour, A.H.H., Ali, M.A., and Ibrahem, Y.M.,Phosphorus, Sulfur Silicon Relat. Elem., 2007, vol. 182, p. 695. https://doi.org/10.1080/10426500601087277

    Article  CAS  Google Scholar 

  7. Chen, H., Zhang, W., Tam, R., and Raney, A.K., Int. Patent Appl. Pub. no. WO2005058315, 2005.

  8. Hoelzemann, G., Graedler, U., Greiner, H., Amendt, C., Musil, D., and Hillertz, P., US Patent no. 8202882, 2012.

  9. Reinhard, E.J., Kolodziej, S.A., Anderson, D.R., Stehle, N.W., Vernier, W.F., Lee, L.F., and Hegde, S.G., US Patent Appl. Pub. no. 20040127519, 2004.

  10. Anderson, D.R., Stehle, N.W., Kolodziej, S.A., Reinhard, E.J., and Lee, L.F., US Patent Appl. Pub. no. 2004142978, 2004.

  11. Anderson, D.R., Stehle, N.W., Kolodziej, S.A., and Reinhard, E.J., Int. Patent Appl. Pub. no. WO2004055015, 2015.

  12. Adams, N.D., Benowitz, A.B., Rueda Benede, M.L., Evans, K.A., Fosbenner, D.T., King, B.W., Li, M., Miller, W.H., Reif, A.J., Romeril, S.P., Schmidt, S.J., and Wiggall, K., Int. Patent Appl. Pub. no. WO2017216726, 2017.

  13. Adams, N.D., Benowitz, A.B., Rueda Benede, M.L., Evans, K.A., Fosbenner, D.T., King, B.W., Li, M., Luengo, J.I., Miller, W.H., Reif, A.J., Romeril, S.P., Schmidt, S.J., Butlin, R.J., Goldberg, K.M., Jordan, A.M., Kershaw, C.S., Raoof, A., and Waszkowycs, B., Int. Patent Appl. Pub. no. WO2017216727, 2017.

  14. Guo, K., Mutter, R., Heal, W., Reddy, T.R.K., Cope, H., Pratt, S., Thompson, M.J., and Chen, B., Eur. J. Med. Chem., 2008, vol. 43, p. 93. https://doi.org/10.1016/j.ejmech.2007.02.018

    Article  CAS  PubMed  Google Scholar 

  15. Vakalopoulos, A., Meibom, D., Albrecht-Kupper, B., Zimmermann, K., Keldenich, J., Lerchen, H.-G., Nell, P., Sussmeier, F., and Krenz, U., US Patent no. 8772498, 2014.

  16. Nell, P., Vakalopoulos, A., Sussmeier, F., Albrecht-Kupper, B., Zimmermann, K., Keldenich, J., and Meibom, D., US Patent no. 8609686, 2013.

  17. Karpov, S.V., Grigor’ev, A.A., Kayukov, Y.S., Karpova, I.V., Nasakin, O.E., and Tafeenko, V.A., J. Org. Chem., 2016, vol. 81, p. 6402. https://doi.org/10.1021/acs.joc.6b01040

    Article  CAS  PubMed  Google Scholar 

  18. Grigor’ev, A.A., Karpov, S.V., Kayukov, Y.S., Belikov, M.Y., and Nasakin, O.E., Tetrahedron Lett., 2015, vol. 56, p. 6279. https://doi.org/10.1016/j.tetlet.2015.09.130

    Article  CAS  Google Scholar 

  19. Grigor’ev, A.A., Karpov, S.V., Kayukov, Y.S., Gracheva, I.A., and Tafeenko, V.A., Synlett, 2017, vol. 28, p. 1592. https://doi.org/10.1055/s-0036-1588823

    Article  CAS  Google Scholar 

  20. Karpov, S.V., Kayukov, Y.S., Bardasov, I.N., Kayukova, O.V., Lipin, K.V., and Nasakin, O.E., Russ. J. Org. Chem., 2011, vol. 47, p. 1492. https://doi.org/10.1134/S107042801110006X

    Article  CAS  Google Scholar 

Download references

Funding

This study was performed under financial support by the Russian Foundation for Basic Research (project no. 18-33-01204 mol_a).

Author information

Authors and Affiliations

  1. I.N. Ul’yanov Chuvash State Universitty, 428015, Cheboksary, Russia

    Ya. S. Kayukov, S. V. Karpov & A. A. Grigor’ev

  2. Chuvash State Agricultural Academy, 428003, Cheboksary, Russia

    O. V. Kayukova

Authors
  1. Ya. S. Kayukov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. V. Karpov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. V. Kayukova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. A. Grigor’ev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to O. V. Kayukova or A. A. Grigor’ev.

Ethics declarations

The authors declare no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kayukov, Y.S., Karpov, S.V., Kayukova, O.V. et al. Synthesis of 4-Acyl-2-amino-6-(arylsulfanyl)pyridine-3,5-dicarbonitriles. Russ J Org Chem 56, 1313–1316 (2020). https://doi.org/10.1134/S1070428020070283

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428020070283

Keywords:

Search

Navigation