Skip to main content
SpringerLink
Log in

New spiro derivative of dihydro-1,2,3-triazolo[1,5-a]pyrimidine as a product of multicomponent reaction

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A new spiro derivative of dihydro-1,2,3-triazolo[1,5-a]pyrimidine – 5'-amino-6'-cyano-4'H-spiro[cyclohexane-1,7'-[1,2,3]triazolo[1,5-a]-pyrimidine]-3'-carboxamide – was prepared by three-component reaction of 5-amino-1,2,3-triazole-4-carboxamide with malononitrile and cyclohexanone; the structure of product was established by X-ray analysis. Microwave activation and conventional heating showed the formation of single product and the same direction of heterocyclization. Available literature data concerning similar reactions using 3-amino-1,2,4-triazole or 2-aminobenzimidazole were reinvestigated experimentally with consideration of alternative structures; structures of products were studied by NMR including NOE experiments.

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 1.
Scheme 2.
Scheme 3.
Figure 1.
Scheme 4.
Scheme 5.
Figure 2.

Similar content being viewed by others

References

  1. Tsuda, Y.; Mishina, T.; Obata, M.; Araki, K.; Inui, J.; Nakamura, T. US Patent 4918074.

  2. Atwal, K. S.; Moreland, S. Bioorg. Med. Chem. Lett. 1991, 1, 291.

    Article  CAS  Google Scholar 

  3. Holladay, M. W.; Carroll, W. A.; Drizin, I.; Yi, L.; Zhang, H. Q. US Patent 6274587.

  4. Magedov, I. V.; Manpadi, M.; Van slambrouck, S.; Steelant, W. F. A.; Rozhkova, E.; Przheval'skii, N. M.; Rogelj, S.; Kornienko, A. J. Med. Chem. 2007, 50, 5183.

    Article  CAS  Google Scholar 

  5. Beck, H. P.; DeGraffenreid, M.; Fox, B.; Allen, J. G.; Rew, Y.; Schneider, S.; Saiki, A. Y.; Yu, D.; Oliner, J. D.; Salyers, K.; Ye, Q.; Olson, S. Bioorg. Med. Chem. Lett. 2011, 21, 2752.

    Article  CAS  PubMed  Google Scholar 

  6. Komykhov, S. A.; Tkachenko, I. G.; Musatov, V. I.; Diachkov, M. V.; Chebanov, V. A.; Desenko, S. M. ARKIVOC 2016, (iv), 277.

  7. Desenko, S. M. Chem. Heterocycl. Compd. 1995, 31, 125. [Khim. Geterotsikl. Soedin. 1995, 147.]

  8. Chebanov, V. A.; Desenko, S. M.; Gurley, T. W. Azaheterocycles Based on α,β-Unsaturated Carbonyls; Springer: Berlin, 2008.

    Google Scholar 

  9. Desenko, S. M.; Orlov, V. D.; Lipson, V. V.; Shishkin, O. V.; Lindeman, S. V.; Struchkov, Yu. T. Chem. Heterocycl. Compd. 1991, 27, 1242. [Khim. Geterotsikl. Soedin. 1991, 1539.]

  10. Desenko, S. M.; Orlov, V. D. Chem. Heterocycl. Compd. 1989, 25, 840. [Khim. Geterotsikl. Soedin. 1989, 1000.]

  11. Desenko, S. M.; Orlov, V. D.; Shishkin, O. V.; Barykin, K. É.; Lindeman, S. V.; Struchkov, Yu. T. Chem. Heterocycl. Compd. 1993, 29, 1163. [Khim. Geterotsikl. Soedin. 1993, 1357.]

  12. Orlov, V. D.; Desenko, S. M.; Potekhin, K. A.; Struchkov, Yu. T. Chem. Heterocycl. Compd. 1988, 24, 192. [Khim. Geterotsikl. Soedin. 1988, 229.]

  13. Desenko, S. M.; Orlov, V. D.; Getmanskii, N. V.; Shishkin, O. V.; Lindeman, S. V.; Struchkov, Yu. T. Chem. Heterocycl. Compd. 1993, 29, 406. [Khim. Geterotsikl. Soedin. 1993, 481.]

  14. Orlov, V. D.; Desenko, S. M.; Pivnenko, N. S. Chem. Heterocycl. Compd. 1988, 24, 1233. [Khim. Geterotsikl. Soedin. 1988, 1489.]

  15. Orlov, V. D.; Kiroga, Kh.; Kolos, N. N.; Desenko, S. M. Chem. Heterocycl. Compd. 1988, 24, 791. [Khim. Geterotsikl. Soedin. 1988, 962.]

  16. Desenko, S. M.; Orlov, V. D. Chem. Heterocycl. Compd. 1989, 25, 894. [Khim. Geterotsikl. Soedin. 1989, 1071.]

  17. Gladkov, E. S.; Gura, K. A.; Sirko, S. M.; Desenko, S. M.; Groth, U.; Chebanov, V. A. Beilstein J. Org. Chem. 2012, 8, 2100.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Gladkov, E. S.; Sirko, S. N.; Shishkina, S. V.; Shishkin, O. V.; Knyazeva, I. V.; Desenko, S. M.; Chebanov, V. A. Monatsh. Chem. 2010, 141, 773.

    Article  CAS  Google Scholar 

  19. Desenko, S. M.; Gladkov, E. S.; Shishkina, S. V.; Shishkin, O. V.; Komykhov, S. A.; Orlov, V. D.; Meier, H. J. Heterocycl. Chem. 2006, 43, 1563.

    Article  CAS  Google Scholar 

  20. Insuasty, B.; Salcedo, A.; Abonia, R.; Quiroga, J.; Nogueras, M.; Sanchez, A. Heterocycl. Commun. 2002, 8, 287.

    CAS  Google Scholar 

  21. Komykhov, S. A.; Ostras, K. S.; Kostanyan, A. R.; Desenko, S. M.; Orlov, V. D.; Meier, H. J. Heterocycl. Chem. 2005, 42, 1111.

    Article  CAS  Google Scholar 

  22. Dandia, A.; Sarawgi, P.; Arya, K.; Khaturia, S. ARKIVOC 2006, (xvi), 83.

  23. Dandia, A.; Singh, R.; Singh, D.; Arya, K. Lett. Org. Chem. 2009, 6, 100.

    Article  CAS  Google Scholar 

  24. Dandia A.; Sarawgi, P.; Bingham, A. L.; Drake, J. E.; Hursthouse, M. B.; Light, M. E.; Ratnani, R. J. Chem. Res. 2007, 155.

  25. Desenko, S. M.; Orlov, V. D.; Éstrada, Kh. Chem. Heterocycl. Compd. 1990, 26, 839. [Khim. Geterotsikl. Soedin. 1990, 999.]

  26. Hoover, J. R. E.; Day, A. R. J. Am. Chem. Soc. 1956, 78, 5832.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. State Scientific Institution “Institute for Single Crystals”, National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv, 61001, Ukraine

    Eugene S. Gladkov, Svetlana M. Sirko, Vladimir I. Musatov, Svetlana V. Shishkina, Irina G. Tkachenko, Sergey A. Komykhov & Sergey M. Desenko

  2. V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61022, Ukraine

    Eugene S. Gladkov, Svetlana V. Shishkina, Sergey A. Komykhov & Sergey M. Desenko

  3. Kharkiv Forensic Science Center, Ministry of Internal Affairs of Ukraine, 32 Kovtuna St., Kharkiv, 61036, Ukraine

    Irina G. Tkachenko

Authors
  1. Eugene S. Gladkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Svetlana M. Sirko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Vladimir I. Musatov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Svetlana V. Shishkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Irina G. Tkachenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Sergey A. Komykhov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Sergey M. Desenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Sergey A. Komykhov.

Additional information

Supplementary information file containing 1H and 13C NMR spectra of compounds 11, 12, and 14, 1D NOE spectra of compound 11, and arrangement of molecules 14 in crystal according to X-ray data is available at the journal website at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(12), 1139–1144

Electronic supplementary material

ESM 1

(PDF 1924 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gladkov, E.S., Sirko, S.M., Musatov, V.I. et al. New spiro derivative of dihydro-1,2,3-triazolo[1,5-a]pyrimidine as a product of multicomponent reaction. Chem Heterocycl Comp 54, 1139–1144 (2018). https://doi.org/10.1007/s10593-019-02405-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02405-9

Keywords

Search

Navigation