Skip to main content
SpringerLink
Log in

Synthesis of 5-(5-amino-1H-pyrazol-1-yl)-1,2,3-thiadiazole-4-carboxylic acid ethyl esters and their cyclization into pyrazolo[1,5-a][1,2,3]thiadiazolo[4,5-e]pyrimidin-4(5H)-ones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A method for the synthesis of novel 1H-pyrazol-1-yl-1,2,3-thiadiazole derivatives has been proposed and their intramolecular cyclization to pyrazolo[1,5-a][1,2,3]thiadiazolo[4,5-e]pyrimidin-4(5H)-ones, previously unknown fused tricyclic heterocycles, has been studied.

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

Figure 1.
Scheme 1.
Figure 2.

Similar content being viewed by others

References

  1. Ferraris, D. V. J. Med. Chem. 2010, 53, 4561.

    Article  CAS  PubMed  Google Scholar 

  2. Virág, L.; Szabó C. Pharmacol. Rev. 2002, 54, 375.

    Article  PubMed  Google Scholar 

  3. Hannigan, K.; Kulkarni, S. S.; Bdzhola, V. G.; Golub, A. G.; Yarmoluk, S. M.; Talele, T. T. Bioorg. Med. Chem. Lett. 2013, 23, 5790.

    Article  CAS  PubMed  Google Scholar 

  4. Wenthur, C. J.; Morrison, R. D.; Daniels, J. S.; Conn, P. J.; Lindsley, C. W. Bioorg. Med. Chem. Lett. 2014, 24, 2693.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Alcaro, S.; Artese, A.; Ortuso, F. In Anticancer Therapeutics; Missailidis, S., Ed.; Wiley-Blackwell, 2008, p. 33.

  6. Zhou, J.; Ji, M.; Yao, H.; Cao, R.; Zhao, H.; Wang, X.; Chen, X.; Xu, B. Org. Biomol. Chem. 2018, 16, 3189.

    Article  CAS  PubMed  Google Scholar 

  7. He, X.; Li, X.-Y.; Liang, J.-W.; Cao, Ch.; Li, Sh.; Zhang, T.-J.; Meng, F.-H. Bioorg. Med. Chem. Lett. 2018, 28, 847.

    Article  CAS  PubMed  Google Scholar 

  8. Almahli, H.; Hadchity, E.; Jaballah, M. Y.; Daher, R.; Ghabbour, H. A.; Kabil, M. M.; Al-shakliah, N. S.; Eldehna, W. M. Bioorg. Chem. 2018, 77, 443.

    Article  CAS  PubMed  Google Scholar 

  9. Zhou, J.; Ji, M.; Zhu, Zh.; Cao, R.; Chen, X.; Xu, B. Eur. J. Med. Chem. 2017, 132, 26.

    Article  CAS  PubMed  Google Scholar 

  10. Voskoboynik, O. Yu.; Kolomoets, O. S.; Palchikov, V. A.; Kovalenko, S. I.; Belenichev, I. F.; Shishkina, S. V. Chem. Heterocycl. Compd. 2017, 53, 1134. [Khim. Geterotsikl. Soedin. 2017, 53, 1134.]

  11. Vysokova, O. A.; Kalinina, T. A.; Tokareva, M. A.; Pospelova, T. A.; Glukhareva, T. V.; Morzherin, Yu. Yu. Chem. Heterocycl. Compd. 2017, 53, 236. [Khim. Geterotsikl. Soedin. 2017, 53, 236.]

  12. Orvieto, F.; Branca, D.; Giomini, C.; Jones, Ph.; Koch, U.; Ontoria, J. M.; Palumbi, M. C.; Rowley, M.; Toniatti, C.; Muraglia, E. Bioorg. Med. Chem. Lett. 2009, 19, 4196.

    Article  CAS  PubMed  Google Scholar 

  13. Shafran, Y.; Glukhareva, T.; Dehaen, W.; Bakulev, V. Adv. Heterocycl. Chem. 2018, 126, 109.

    Article  Google Scholar 

  14. Morzherin, Yu. Yu.; Glukhareva, T. V.; Bakulev, V. A. Chem. Heterocycl Compd. 2003, 39, 679. [Khim. Geterotsikl. Soedin. 2003, 803.]

  15. Gupta, S.; Rodrigues, L. M.; Esteves, A. P.; Oliveira-Campos, A. M. F.; Nascimento, M. S. J.; Nazareth, N.; Cidade, H.; Neves, M. P.; Fernandes, E.; Pinto, M.; Cerqueira, N. M. F. S. A.; Brás, N. Eur. J. Med. Chem. 2008, 43, 771.

    Article  CAS  PubMed  Google Scholar 

  16. Shamroukh, A. H.; Rashad, A. E.; Ali, H. S.; Awad, S. M. J. Heterocycl. Chem. 2014, 51, 899.

    Article  CAS  Google Scholar 

  17. Morzherin, Yu. Yu.; Tarasov, E. V.; Bakulev, V. A. Chem. Heterocycl. Compd. 1994, 30, 489. [Khim. Geterotsikl. Soedin. 1994, 554.]

  18. Borisova, I. A.; Zubarev, A. A.; Rodinovskaya, L. A.; Shestopalov, A. M. ARKIVOC 2017, (iii), 73.

  19. Gorobets, N. Yu.; Tkachova, V. P.; Tkachov, R. P.; Dyachenko, O. D.; Rusanov, E. B.; Dyachenko, V. D. ARKIVOC, 2010, (xi), 254.

  20. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.

    Article  CAS  Google Scholar 

  21. Palatinus, L.; Chapuis, G. J. Appl. Crystallogr. 2007, 40, 786.

    Article  CAS  Google Scholar 

  22. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

    Article  CAS  Google Scholar 

Download references

This work was supported by the Russian Science Foundation (grant 16-16-04022). 1H and 13С NMR spectra were registered in the

Laboratory of Complex Studies and Expert Evaluation of Organic Materials at the Center for Collective Use of the Ural Federal University.

Author information

Authors and Affiliations

  1. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg, 620002, Russia

    Olga А. Vysokova, Tatiana A. Kalinina, Tatiana А. Pospelova, Konstantin L. Obydennov & Tatiana V. Glukhareva

  2. I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Science, 22 S. Kovalevskoi St. / 20 Akademicheskaya St., Yekaterinburg, 620990, Russia

    Pavel А. Slepukhin & Tatiana V. Glukhareva

Authors
  1. Olga А. Vysokova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tatiana A. Kalinina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pavel А. Slepukhin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tatiana А. Pospelova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Konstantin L. Obydennov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Tatiana V. Glukhareva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Tatiana V. Glukhareva.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(11), 1079–1082

Electronic supplementary material

ESM 1

(PDF 1132 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Vysokova, O.А., Kalinina, T.A., Slepukhin, P.А. et al. Synthesis of 5-(5-amino-1H-pyrazol-1-yl)-1,2,3-thiadiazole-4-carboxylic acid ethyl esters and their cyclization into pyrazolo[1,5-a][1,2,3]thiadiazolo[4,5-e]pyrimidin-4(5H)-ones. Chem Heterocycl Comp 54, 1079–1082 (2018). https://doi.org/10.1007/s10593-018-2396-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-018-2396-6

Keywords

Search

Navigation