Skip to main content
Log in

Synthesis and Spectral, Electrochemical, and Antioxidant Properties of 2-(5-Aryl-6-R-3-phenyl-5,6-dihydro-4H-1,2,4,5-tetrazin-1-yl)-1,3-benzothiazoles

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

Abstract

New 2-(5-aryl-6-R-3-phenyl-5,6-dihydro-4H-1,2,4,5-tetrazin-1-yl)-1,3-benzothiazoles were synthesized from the corresponding formazans by alkylation and subsequent cyclization of N-alkyl derivatives. The products were characterized by 1H and 13C NMR, IR, and mass spectra and X-ray diffraction data. Electrochemical properties and antioxidant activity of the synthesized benzothiazole derivatives were studied.

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. Valko, M., Leibfritz, D., Moncol, J., Cronin, M.T.D., Mazur, M., and Telser, J., Int. J. Biochem. Cell Biol., 2007, vol. 39, p. 44. https://doi.org/10.1016/j.biocel.2006.07.001

    Article  CAS  Google Scholar 

  2. Ai Pham-Huy, L., He, H., and Pham-Huy, C., Int. J. Biomed. Sci., 2008, vol. 4, p. 89.

    Google Scholar 

  3. Hussain, H.H., Babic, G., Durst, T., Wright, J., Flueraru, M., Chichirau, A., and Chepelev, L.L., J. Org. Chem., 2003, vol. 68, p. 7023. https://doi.org/10.1021/jo0301090

    Article  CAS  Google Scholar 

  4. Sarbu, C. and Casoni, D., Cent. Eur. J. Chem., 2013, vol. 11, p. 679. https://doi.org/10.2478/s11532-013-0210-y

    CAS  Google Scholar 

  5. Nikolaeva, N.S., Soldatova, Yu.V., Smolina, A.V., Aksinenko, A.Yu., Sokolov, V.B., Kinzirsky, A.S., Kotel’nikova, R.A., Shtolko, V.N., and Kotel’nikov, A.I., Russ. Chem. Bull., Int. Ed., 2017, vol. 66, p. 870. https://doi.org/10.1007/s11172-017-1821-9

    Article  CAS  Google Scholar 

  6. Milaeva, E.Z., Shpakovsky, D.B., Maklakova, I.A., Zufanov, K.A., Neganova, M.E., Shevtsova, E.F., Churakov, A.V., Babkova, V.A., Babkov, D.A., Kosolapov, V.A., and Spasov, A.A., Russ. Chem. Bull., Int. Ed., 2018, vol. 67, p. 2025. https://doi.org/10.1007/s11172-018-2324-z

    Article  CAS  Google Scholar 

  7. El-Mekabaty, A. and El-Shora, H.M., Chem. Heterocycl. Compd., 2018, vol. 54, p. 618. https://doi.org/10.1007/s10593-018-2317-8

    Article  CAS  Google Scholar 

  8. Makhaeva, G.F., Lushchekina, S.V., Boltneva, N.P., Serebryakova, O.G., Rudakova, E.V., Ustyugov, A.A., Bachurin, S.O., Shchepochkin, A.V., Chupakhin, O.N., Charushin, V.N., and Richardson, R.J., Bioorg. Med. Chem., 2017, vol. 25, p. 5981. https://doi.org/10.1016/j.bmc.2017.09.028

    Article  CAS  Google Scholar 

  9. Kozlova, Z.G., Shchipanov, V.P., and Tsepalov, V.F., Zh. Org. Khim., 1980, vol. 16, p. 1098.

    CAS  Google Scholar 

  10. Ol’khovikova, N.B., Rusinova, L.I., Shmelev, L.V., Lipunova, G.N., Klyuev, N.A., and El’tsov, A.V., Zh. Obshch. Khim., 1988, vol. 58, p. 1626.

    Google Scholar 

  11. Fedorchenko, T.G., Lipunova, G.N., Shchepochkin, A.V., Tsmokalyuk, A.N., Slepukhin, P.A., and Chupakhin, O.N., Mendeleev Commun., 2018, vol. 28, p. 297. https://doi.org/10.1016/j.mencom.2018.05.023

    Article  CAS  Google Scholar 

  12. McConnachie, G. and Neugebauer, F.A., Tetrahedron, 1975, vol. 31, p. 555. https://doi.org/10.1016/0040-4020(75)85029-0

    Article  CAS  Google Scholar 

  13. Barilone, J. and Neese, F., Appl. Magn. Reson., 2015, vol. 46, p. 117. https://doi.org/10.1007/s00723-014-0627-2

    Article  CAS  Google Scholar 

  14. Neese, F., Wiley Interdiscip. Rev.: Comput. Mol. Sci., 2012, vol. 2, p. 73. https://doi.org/10.1002/wcms.81

    CAS  Google Scholar 

  15. Stol, S. and Schweiger, A., J. Magn. Reson., 2006, vol. 178, p. 42. https://doi.org/10.1016/j.jmr.2005.08.013

    Article  Google Scholar 

  16. Neugebauer, F.A., Otting, W., Smith, H.O., and Trischmann, H., Eur. J. Inorg. Chem., 1972, vol. 105, p. 549. https://doi.org/10.1002/cber.19721050220

    CAS  Google Scholar 

  17. Shchipanov, V.P. and Klyuev, N.A., Chem. Heterocycl. Compd., 1981, vol. 17, p. 1145. https://doi.org/10.1007/BF00506470

    Article  Google Scholar 

  18. Schnakenburg, G. and Meyer, A., Acta Crystallogr., Sect. E, 2018, vol. 74, p. 292. https://doi.org/10.1107/S2056989018001913

    Article  CAS  Google Scholar 

  19. Sharma, O.P. and Bhat, T.K., Food Chem., 2009, vol. 113, p. 1202. https://doi.org/10.1016/j.foodchem.2008.08.008

    Article  CAS  Google Scholar 

  20. Sheldrick, G.M., Acta Crystallogr, Sect. A, 2008, vol. 64, p. 112. https://doi.org/10.1107/S0108767307043930

    Article  CAS  Google Scholar 

  21. Klyuev, N.A., Zhil’nikov, V.G., Aleksandrov, G.G., Grandberg, I.I., and Lipunova, G.N., Zh. Org. Khim., 1983, vol. 19, p. 2615.

    CAS  Google Scholar 

  22. Fedorchenko, T.G., Lipunova, G.N., Shchepochkin, A.V., Tsmokalyuk, A.N., Valova, M.S., and Slepukhin, P.A., Chem. Heterocycl. Compd., 2019, vol. 55, p. 560. https://doi.org/10.1007/s10593-019-02496-4

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The spectral and analytical data were obtained using the facilities of the Spectroscopy and Analysis of Organic Compounds joint center at the Postovskii Institute of Organic Synthesis (Ural Branch, Russian Academy of Sciences).

Funding

This study was performed in the framework of state assignment (project nos. AAAA-A19-119012290117-6, AAAA-A19-119012490006-1, AAA-A19-119011790130-3) and under financial support by the Ural Branch, Russian Academy of Sciences (project no. 18-3-3-16).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to T. G. Fedorchenko.

Ethics declarations

The authors declare the absence of conflict of interest.

Additional information

Russian Text © The Author(s), 2020, published in Zhurnal Organicheskoi Khimii, 2020, Vol. 56, No. 1, pp. 52–64.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Fedorchenko, T.G., Lipunova, G.N., Shchepochkin, A.V. et al. Synthesis and Spectral, Electrochemical, and Antioxidant Properties of 2-(5-Aryl-6-R-3-phenyl-5,6-dihydro-4H-1,2,4,5-tetrazin-1-yl)-1,3-benzothiazoles. Russ J Org Chem 56, 38–48 (2020). https://doi.org/10.1134/S1070428020010078

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428020010078

Keywords

Navigation