Skip to main content
SpringerLink
Log in

Efficient Synthesis of 5-[3(4)-(5-Phenyl-1,3,4-oxаdiаzol-2-yl)­anilino]-1,2,4-triаzines

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

Abstract

1,2,4-Triazine derivatives containing a 3- or 4-(5-phenyl-1,3,4-oxadiazol-2-yl)anilino group on C5 were synthesized by nucleophilic substitution of the cyano group in 3,6-diaryl-1,2,4-triazine-5-carbonitriles under solvent-free conditions.

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

Scheme

REFERENCES

  1. Baijika, P., Akash, M., Midhula, C.C., and Shadiha, S.K., Int. J. Adv. Res., 2018, vol. 6, p. 1114. https://doi.org/10.21474/IJAR01/6328

    Article  Google Scholar 

  2. Nayak, S.G. and Poojary, B., Chem. Afr., 2019, vol. 2, p. 551. https://doi.org/10.1007/s42250-019-00084-9

    Article  CAS  Google Scholar 

  3. Pitasse-Santos, P., Sueth-Santiago, V., and Lima, M.E.F., J. Braz. Chem. Soc., 2018, vol. 29, p. 435. https://doi.org/10.21577/0103-5053.20170208

    Article  CAS  Google Scholar 

  4. Misra, U., Hitkari, A., Sexena, A.K., Gurtur, S., and Shenker, K., Eur. J. Med. Chem., 1996, vol. 31, p. 629. https://doi.org/10.1016/0223-5234(96)89559-6

    Article  CAS  Google Scholar 

  5. Kumar, D., Sundaree, S., Johnson, E.O., and Shah, K., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 4492. https://doi.org/10.1016/j.bmcl.2009.03.172

    Article  CAS  PubMed  Google Scholar 

  6. Ergun, Y., Orhan, O.F., Ozer, U.G., and Gisi, G., Eur. J. Pharmacol., 2010, vol. 630, p. 74. https://doi.org/10.1016/j.ejphar.2009.12.021

    Article  CAS  PubMed  Google Scholar 

  7. Kumar, K.A., Jayaroopa, P., and Kumar, G.V., Int. J. ChemTech. Res., 2012, vol. 4, p. 1782.

    Google Scholar 

  8. Liao, B.-R., He, H.-B., Yang, L.-L., Gao, L.-X., Chang, L., Tang, J., Li, J.-Y., Li, J., and Yang, F., Eur. J. Med. Chem., 2014, vol. 83, p. 15. https://doi.org/10.1016/j.ejmech.2014.06.011

    Article  CAS  PubMed  Google Scholar 

  9. Kwak,, Y.-S. and Coppola, G.M., Int. Patent Appl. Pub. no. WO2009040410 A1, 2009; Chem. Abstr., 2009, vol. 150, no. 374536

  10. Abdula, Y., Gao, L., He, H., He, Y., Li, J., Li, J., Tang, J., Yang, F., and Yang, L., CN Patent no. CN104098526A, 2014; Chem. Abstr., 2014, vol. 161, no. 647230.

  11. Sindhe, M.A., Bodke, Y.D., Kenchappa, R., Telkar, S., and Chandrashekar, A., J. Chem. Biol., 2016, vol. 9, p. 79. https://doi.org/10.1007/s12154-016-0153-9

    Article  PubMed  PubMed Central  Google Scholar 

  12. Arshad, M., Khan, T.A., and Khan, M.A., Int. J. Pharm. Sci. Res., 2014, vol. 5, p. 149.

    Google Scholar 

  13. Srinivasa Rao, D., Pavan Kumar, G.V., Pooja, B., Harika, G., Anil Kumar, Y., and Sadasiva Rao, G., Chem. Sin., 2016, vol. 7, p. 101.

    Google Scholar 

  14. Shchegol’kov, E.V., Khudina, O.G., Ivanova, A.E., Burgart, Ya.V., Sadchikova, E.V., Kravchenko, M.A., and Saloutin, V.I., Pharm. Chem. J., 2014, vol. 48, p. 383. https://doi.org/10.1007/s11094-014-1115-6

    Article  CAS  Google Scholar 

  15. Huang, J.J., J. Org. Chem., 1985, vol. 50, p. 2293. https://doi.org/10.1021/jo00213a019

    Article  CAS  Google Scholar 

  16. Kozhevnikov, D.N., Kozhevnikov, V.N., Kovalev, I.S., Rusinov, V.L., Chupakhin, O.N., and Aleksandrov, G.G., Russ. J. Org. Chem., 2002, vol. 38, p. 744. https://doi.org/10.1023/A:1019631610505

    Article  CAS  Google Scholar 

  17. Rykowski, A., Branowska, D., Makosza, M., and Van Ly, P., J. Heterocycl. Chem., 1996, vol. 33, p. 1567. https://doi.org/10.1002/jhet.5570330603

    Article  CAS  Google Scholar 

  18. Ohba, S., Konno, S., and Yamanaka, H., Chem. Pharm. Bull., 1991, vol. 39, p. 486. https://doi.org/10.1248/cpb.39.486

    Article  CAS  Google Scholar 

  19. Kozhevnikov, D.N., Kovalev, I.S., Prokhorov, A.M., Rusinov, V.L., and Chupakhin, O.N., Russ. Chem. Bull., Int. Ed., 2003, vol. 52, p. 1588. https://doi.org/10.1023/A:1025601311393

    Article  CAS  Google Scholar 

  20. Kopchuk, D.S., Chepchugov, N.V., Kovalev, I.S., Santra, S., Rahman, M., Giri, K., Zyryanov, G.V., Majee, A., Charushin, V.N., and Chupakhin, O.N., RSC Adv., 2017, vol. 7, p. 9610. https://doi.org/10.1039/c6ra26305d

    Article  CAS  Google Scholar 

  21. Kopchuk, D.S., Starnovskaya, E.S., Shtaitz, Ya.K., Khasanov, A.F., Kim, G.A., Nosova, E.V., Krinoch­kin, A.P., Zyryanov, G.V., Rusinov, V.L., and Chupa­khin, O.N., Res. Chem. Intermed., 2020, vol. 46, p. 3929. https://doi.org/10.1007/s11164-020-04182-z

    Article  CAS  Google Scholar 

  22. Kopchuk, D.S., Shtaitz, Ya.K., Savchuk, M.I., Starnovskaya, E.S., Nosova, E.V., Taniya, O.S., Zyryanov, G.V., Rusinov, V.L., and Chupakhin, O.N., AIP Conf. Proc., 2020, vol. 2280, article ID 040025. https://doi.org/10.1063/5.0018683

  23. Rammohan, A., Reddy, G.M., Krinochkin, A.P., Kopchuk, D.S., Savchuk, M.I., Shtaitz, Ya.K., Zyrya­nov, G.V., Rusinov, V.L., and Chupakhin, O.N., Synth. Commun., 2021, vol. 51, p. 256. https://doi.org/10.1080/00397911.2020.1823993

    Article  CAS  Google Scholar 

  24. Krinochkin, A.P., Guda, M.R., Kopchuk, D.S., Shtaitz, Ya.K., Starnovskaya, E.S., Savchuk, M.I., Rybakova, S.S., Zyryanov, G.V., and Chupakhin, O.N., Russ. J. Org. Chem., 2021, vol. 57, p. 675. https://doi.org/10.1134/S1070428021040278

    Article  CAS  Google Scholar 

  25. Bebbington, D., Binch, H., Charrier, J.-D., Everitt, S., Golec, J., Kay, D., Knegtel, R., Miller, A., and Pierard, F., US Patent Appl. Pub. no. 20040009981 A1, 2004; Chem. Abstr., 2003, vol. 139, no. 255408.

  26. Davis, R.L., Herbert, M.R., Hoffman, T.Z., Kahra­man, M., Pinkerton, A.B., and Thayer, A.M., Int. Patent Appl. Pub. No. WO2007011721 A1, 2007; Chem. Abstr., 2007, vol. 146, no. 184500.

  27. Chupakhin, O.N., Rusinov, V.L., Ulomsky, E.N., Kojevnikov, D.N., and Neunhoeffer, H., Mendeleev Commun., 1997, vol. 7, p. 66. https://doi.org/10.1070/MC1997v007n02ABEH000700

    Article  Google Scholar 

  28. Blackhall, A., Brydon, D.L., Saga, A.J.G., and Smith, D.M., J. Chem. Soc., Perkin Trans. 2, 1980, p. 773. https://doi.org/10.1039/P29800000773

  29. Zavareh, E.R., Hedayati, M., Rad, L.H., Kiani, A., Shahhosseini, S., Faizi, M., and Tabata­bai, S.A., Lett. Drug Des. Discovery, 2014, vol. 11, p. 721. https://doi.org/10.2174/1570180811666140220005530

    Article  CAS  Google Scholar 

  30. Starnovskaya, E.S., Savchuk, M.I., Shtaitz, Ya.K., Kop­chuk, D.S., Kovalev, I.S., Taniya, O.S., Pavlyuk, D.E., Khasanov, A.F., Zyryanov, G.V., and Chupakhin, O.N., Russ. J. Org. Chem., 2020, vol. 56, p. 335. https://doi.org/10.1134/S1070428020010268

    Article  CAS  Google Scholar 

Download references

Funding

This study was performed under financial support by the Council for Grants at the President of the Russian Federation (project no. MD-167.2021.1.3).

Author information

Authors and Affiliations

  1. Yeltsin Ural Federal University, 620002, Yekaterinburg, Russia

    А. P. Krinochkin, M. R. Guda, D. S. Kopchuk, N. V. Slovesnova, I. S. Kovalev, M. I. Savchuk, Ya. K. Shtaitz, E. S. Starnovskaya, G. V. Zyryanov & O. N. Chupakhin

  2. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 620990, Yekaterinburg, Russia

    А. P. Krinochkin, D. S. Kopchuk, N. V. Slovesnova, M. I. Savchuk, E. S. Starnovskaya, G. V. Zyryanov & O. N. Chupakhin

  3. Ural State Medical University, Ministry of Healthcare of the Russian Federation, 620028, Yekaterinburg, Russia

    N. V. Slovesnova

Authors
  1. А. P. Krinochkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. R. Guda
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. D. S. Kopchuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. V. Slovesnova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. I. S. Kovalev
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. M. I. Savchuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Ya. K. Shtaitz
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. E. S. Starnovskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. G. V. Zyryanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. O. N. Chupakhin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to G. V. Zyryanov.

Ethics declarations

The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 10, pp. 1496–1500 https://doi.org/10.31857/S0514749221100177.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Krinochkin, А.P., Guda, M.R., Kopchuk, D.S. et al. Efficient Synthesis of 5-[3(4)-(5-Phenyl-1,3,4-oxаdiаzol-2-yl)­anilino]-1,2,4-triаzines. Russ J Org Chem 57, 1753–1756 (2021). https://doi.org/10.1134/S1070428021100262

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428021100262

Keywords:

Search

Navigation