Skip to main content
SpringerLink
Log in

Synthesis of 4-hydrazinyl-1,6-dihydropyrazolo[3,4-e][1,4]diazepines and their hydrolytic recyclization to 5-amino-4-(1,2,4-triazin-3-yl)-1H-pyrazoles

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

Abstract

4-Hydrazinyl-1,6-dihydropyrazolo[3,4-e][1,4]diazepines were synthesized by reaction of 4-methylsulfanyl- or 4-chloro-5,6-dihydropyrazolo[3,4-e][1,4]diazepines with hydrazine hydrate. Their hydrolytic recyclization afforded 5-amino-4-(1,2,4-triazin-3-yl)-1H-pyrazoles.

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. Ramajayam, R., Girdhar, R., and Yadav, M.R., Mini-Rev. Med. Chem., 2007, vol. 7, p. 793.

    Article  CAS  Google Scholar 

  2. Insuasty, B., Ramirez, J., Becerra, D., Echeverry, C., Quiroga, J., Abonia, R., Robledo, S.M., Velez, I.D., Upegui, Y., Munoz, J.A., Ospina, V., Nogueras, M., and Cobo, J., Eur. J. Med. Chem., 2015, vol. 93, p. 401.

    Article  CAS  Google Scholar 

  3. Pertejo, P., Garcia-Valverde, M., Pena, P., Cordero, N.A., Torroba, T., and Gonzalez-Ortega, A., Org. Biomol. Chem., 2014, vol. 12, p. 4905.

    Article  CAS  Google Scholar 

  4. El-Subbagh, H.I., Hassan, G.S., El-Messery, S.M., Al-Rashood, S.T., Al-Omary, F.A.M., Abulfadl, Y.S., and Shabayek, M.I., Eur. J. Med. Chem., 2014, vol. 74, p. 234.

    Article  CAS  Google Scholar 

  5. Hernandez, S., Moreno, I., SanMartin, R., Herrero, M.T., and Dominguez, E., Org. Biomol. Chem., 2011, vol. 9, p. 2251.

    Article  CAS  Google Scholar 

  6. Bol’but, A.V., Kemskii, S.V., and Vovk, M.V., Russ. J. Org. Chem., 2012, vol. 48, p. 991.

    Article  Google Scholar 

  7. Bol’but, A.V., Kemskii, S.V., and Vovk, M.V., Russ. J. Org. Chem., 2014, vol. 50, p. 685.

    Article  Google Scholar 

  8. Kemskii, S.V., Bol’but, A.V., and Vovk, M.V., J. Org. Pharm. Chem., 2014, vol. 12, no. 2, p. 27.

    Google Scholar 

  9. Tantravedi, S., Chakraborty, S., Shah, H.N., Fishbein, J.C., and Hosmane, R.S., Bioorg. Med. Chem., 2013, vol. 21, p. 4893.

    Article  CAS  Google Scholar 

  10. Zhang, W., Han, R.-B., Zhang, W.-B., Jiang, R.-S., and Piao, F.-Y., J. Heterocycl. Chem., 2013, vol. 50, p. 29.

    Article  Google Scholar 

  11. Wu, Y., Ma, L.-X., Niu, T.-W., Meng, F.-L., Cui, X., and Piao, H.-P., Arch. Pharm., 2012, vol. 345, p. 980.

    Article  CAS  Google Scholar 

  12. Zheng, Y., Bian, M., Deng, X.-Q., Wang, S.-B., and Quan, Z.-S., Arch. Pharm., 2013, vol. 346, p. 119.

    Article  CAS  Google Scholar 

  13. Galal, S.A., Abdelsamie, A.S., Soliman, S.M., Mortier, J., Wolber, G., Ali, M.M., Tokuda, H., Suzuki, N., Lida, A., Ramadan, R.A., and El Diwani, H.I., Eur. J. Med. Chem., 2013, vol. 69, p. 115.

    Article  CAS  Google Scholar 

  14. Bahashwan, S.A., Fayed, A.A., Amr, A.E., Flefel, E.M., and Kalmouch, A., Molecules, 2013, vol. 18, p. 15051.

    Article  CAS  Google Scholar 

  15. Moulin, A., Bibian, M., Blayo, A., El Habrousi, S., Martinez, J., and Ferentz, J.A., Chem. Rev., 2010, vol. 110, p. 1809.

    Article  CAS  Google Scholar 

  16. Reddy, T.R., Li, C., Fisher, P.M., and Dekker, L.V., Chem. Med. Chem., 2012, vol. 7, p. 1435.

    Article  CAS  Google Scholar 

  17. Saad, H.A., Youssef, M.M., and Mosselhi, M.A., Molecules, 2011, vol. 16, p. 4937.

    Article  CAS  Google Scholar 

  18. Olson, J.P., Gichinga, M.G., Butolla, E., Navarro, H.A., Gilmour, B.P., and Carrol, F.I., Org. Biomol. Chem., 2011, vol. 9, p. 4276.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, Kiev, 02660, Ukraine

    S. V. Kemskii, A. V. Bol’but & M. V. Vovk

Authors
  1. S. V. Kemskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Bol’but
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. V. Vovk
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. V. Vovk.

Additional information

Original Russian Text © S.V. Kemskii, A.V. Bol’but, M.V. Vovk, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 10, pp. 1510–1516.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kemskii, S.V., Bol’but, A.V. & Vovk, M.V. Synthesis of 4-hydrazinyl-1,6-dihydropyrazolo[3,4-e][1,4]diazepines and their hydrolytic recyclization to 5-amino-4-(1,2,4-triazin-3-yl)-1H-pyrazoles. Russ J Org Chem 51, 1481–1487 (2015). https://doi.org/10.1134/S107042801510022X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042801510022X

Keywords

Search

Navigation