Skip to main content
SpringerLink
Log in

Synthesis and Transformations of 8,8′-(1,4-Dihydro-1,2,4,5-tetrazine-3,6-diyl)- bis[7-R-3-tert-butylpyrazolo[5,1-c][1,2,4]triazin-4(6H)-ones]

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

Abstract

New 8,8′-(1,4-dihydro-1,2,4,5-tetrazine-3,6-diyl)bis[7-R-3-tert-butylpyrazolo[5,1-c][1,2,4]triazin- 4(6H)-ones] (R = H, NH2, NHAc) were synthesized by reaction of 3-tert-butyl-4-oxo-1,4-dihydropyrazolo- [5,1-c][1,2,4]triazine-8-carbonitriles with hydrazine. Diazotization of the title compounds was accompanied by opening of the tetrazine ring with the formation of pyrazolo[5,1-c][1,2,4]triazine-8-carbonyl azides.

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. Hajos, G. and Riedl, Z., Comprehensive Heterocyclic Chemistry III, Katritzky, A.R., Ramsden, C.A., Scriven, E.F.V., and Taylor, R.J.K., Eds., Amsterdam: Elsevier 2008, vol. 11, p. 765.

    Article  Google Scholar 

  2. Rusinov, V.L., Ulomskii, E.N., Chupakhin, O.N., and Charushin, V.N., Russ. Chem. Bull., Int. Ed. 2008, vol. 57, no. 5, p. 985.

    Article  CAS  Google Scholar 

  3. Guerrini, G., Ciciani, G., Bruni, F., Selleri, S., Melani, F., Daniele, S., Martini, C., and Costanzo, A., Bioorg. Med. Chem. 2011, vol. 19, p. 3074.

    Article  CAS  PubMed  Google Scholar 

  4. Mironovich, L.M. and Kostina, M.V., Chem. Heterocycl. Compd. 2012, vol. 47, no. 10, p. 1286.

    Article  CAS  Google Scholar 

  5. Ivanov, S.M., Mironovich, L.M., Rodinovskaya, L.A., and Shestopalov, A.M., Russ. Chem. Bull., Int. Ed. 2017, vol. 66, no. 6, p. 1126.

    Article  CAS  Google Scholar 

  6. Krivopalov, V.P., Bushuev, M.B., Gatilov, Yu.V., and Shkurko, O.P., Russ. Chem. Bull., Int. Ed. 2010, vol. 59, no. 9, p. 1808.

    Article  CAS  Google Scholar 

  7. El-Barbary, A.A., El-Badawi, M.A., and Loksha, Y.M., J. Heterocycl. Chem., 2001, vol. 38, p. 711.

    Article  CAS  Google Scholar 

  8. Mironovich, L.M. and Kostina, M.V., CCDC 884140: Experimental Crystal Structure Determination, 2016. doi 10.5517/ccdc.csd.ccyp0n8

    Google Scholar 

  9. Ivanov, S.M., Mironovich, L.M., Rodinovskaya, L.A., and Shestopalov, A.M., Russ. Chem. Bull., Int. Ed. 2017, vol. 66, no. 4, p. 727.

    Article  CAS  Google Scholar 

  10. Mironovich, L.M. and Podol’nikova, A.Yu., Russ. J. Org. Chem. 2016, vol. 52, p. 453.

    Article  CAS  Google Scholar 

  11. Mironovich, L.M., Kostina, M.V., and Podol’nikova, A.Yu., Russ. J. Org. Chem. 2013, vol. 49, p. 758.

    Article  CAS  Google Scholar 

  12. Robins, L.I., Carpenter, R.D., Fettinger, J.C., Haddadin, M.J., Tinti, D.S., and Kurth, M.J., J. Org. Chem., 2006, vol. 71, no. 6, p. 2480.

    Article  CAS  PubMed  Google Scholar 

  13. Ivanov, S.M., Mironovich, L.M., Rodinovskaya, L.A., and Shestopalov, A.M., Tetrahedron Lett. 2017, vol. 58, no. 19, p. 1851.

    Article  CAS  Google Scholar 

  14. Fraser, W., Comprehensive Heterocyclic Chemistry III, Katritzky, A.R., Ramsden, C.A., Scriven, E.F.V., and Taylor, R.J.K., Eds., Amsterdam: Elsevier 2008, vol. 6, p. 425.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Southwest State University, ul. 50 let Oktyabrya 94, Kursk, 305040, Russia

    L. M. Mironovich

  2. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii pr. 47, Moscow, 119991, Russia

    S. M. Ivanov & E. D. Daeva

Authors
  1. L. M. Mironovich
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. M. Ivanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. D. Daeva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to L. M. Mironovich.

Additional information

Original Russian Text © L.M. Mironovich, S.M. Ivanov, E.D. Daeva, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 12, pp. 1811–1816.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mironovich, L.M., Ivanov, S.M. & Daeva, E.D. Synthesis and Transformations of 8,8′-(1,4-Dihydro-1,2,4,5-tetrazine-3,6-diyl)- bis[7-R-3-tert-butylpyrazolo[5,1-c][1,2,4]triazin-4(6H)-ones]. Russ J Org Chem 54, 1825–1830 (2018). https://doi.org/10.1134/S1070428018120151

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428018120151

Search

Navigation