Skip to main content
Log in

A regioselective synthesis of imidazothiazolotriazines based on the cyclization of imidazotriazinethiones with phenacyl bromides

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Novel imidazothiazolotriazines were obtained as a result of the reaction of imidazo[4,5-e][1,2,4]triazine-3-thiones with various phenacyl bromides. It was shown that the cyclocondensation proceeds with high regioselectivity leading to the formation of linear 7-arylimidazo-[4,5-e]thiazolo[3,2-b][1,2,4]triazines.

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.

Figure 1.
Figure 2.
Figure 3.

Similar content being viewed by others

References

  1. (a) de Souza, M. V. N. J. Sulfur Chem. 2005, 26, 429. (b) Tomašić, T.; Mašič, L. P. Curr. Med. Chem. 2009, 16, 1596. (c) Ali, S. H.; Sayed, A. R. Synth. Commun. 2021, 51, 670. (d) Chhabria, M. T.; Patel, S.; Modi, P.; Brahmkshatriya, P. S. Curr. Top. Med. Chem. 2016, 16, 2841.

  2. (a) Fleming, A. Lancet 1943, 242, 434. (b) Eagle, H. J. Bacteriol. 1946, 52, 81.

  3. Igual-Adell, R.; Oltra-Alcaraz, C. Expert Opin. Pharmacother. 2004, 5, 2615.

    Article  CAS  PubMed  Google Scholar 

  4. Hotta, N. Biomed. Pharmacother. 1995, 49, 232.

    Article  CAS  PubMed  Google Scholar 

  5. Ye, X.; Zhou, W.; Li, Y.; Sun, Y.; Zhang, Y.; Ji, H.; Lai, Y. Cancer Chemother. Pharmacol. 2010, 66, 277.

    Article  CAS  PubMed  Google Scholar 

  6. Cai, D.; Li, T.; Xie, Q.; Yu, X.; Xu, W.; Chen, Y.; Jin, Z.; Hu, C. Molecules 2020, 25, 1307.

    Article  CAS  PubMed Central  Google Scholar 

  7. (a) Abdel-Rahman, R. M.; Seada, M.; Fawzy, M.; El-Baz, I. Pharmazie 1994, 49, 729. (b) Liu, K. C.; Shih, B. J.; Lee, C. H. J. Heterocycl. Chem. 1992, 29, 97.

  8. (a) Izmest'ev, A. N.; Anikina, L. V.; Zanin, I. E.; Kolotyrkina, N. G.; Izmalkova, E. S.; Kravchenko, A. N.; Gazieva, G. A. New J. Chem. 2022, 24, 11632. (b) Izmest'ev, A. N.; Gazieva, G. A.; Anikina, L. V.; Pukhov, S. A.; Karnoukhova, V. A.; Kolotyrkina, N. G.; Kravchenko, A. N. New J. Chem. 2021, 45, 12271. (c) Gazieva, G. A.; Izmest'ev, A. N.; Anikina, L. V.; Pukhov, S. A.; Meshchaneva, M. E.; Khakimov, D. V.; Kolotyrkina, N. G.; Kravchenko, A. N. Mol. Diversity 2018, 22, 585. (d) Izmest'ev, A. N.; Gazieva, G. A.; Kulikov, A. S.; Anikina, L. V.; Kolotyrkina, N. G.; Kravchenko, A. N. Rus. J. Org. Chem. 2017, 53, 753.

  9. (a) Khalilpour, A.; Asghari, S.; Pourshab, M. Chem. Biodiversity 2019, 16, e1800563. (b) Izmest'ev, A. N.; Vinogradov, D. B.; Kolotyrkina, N. G.; Kravchenko, A. N.; Gazieva, G. A. Beilstein J. Org. Chem. 2021, 17, 1141.

  10. Kushakova, P. M.; Yulisova, A. I.; Ramsh, S. M.; Garabadgiu, A. V. Chem. Heterocycl. Compd. 2006, 42, 520.

    Article  CAS  Google Scholar 

  11. Hantzsch, A.; Traumann, V. Ber. Dtsch. Chem. Ges. 1888, 21, 938.

    Article  Google Scholar 

  12. (a) Ulrich, H.; Sayigh, A. A. R. J. Org. Chem. 1965, 30, 2781. (b) Faidallah, H. M.; Khan, K. A.; Asiri, A. M. J. Fluorine Chem. 2011, 132, 870.

  13. (a) Boga, C.; Forlani, L.; Silvestroni, C.; Bonamartini Corradi, A.; Sgarabotto, P. J. Chem. Soc., Perkin Trans. 1 1999, 10, 1363. (b) Bramley, S. E.; Dupplin, V.; Goberdhan, D. G. C.; Meakins, G. D. J. Chem. Soc., Perkin Trans. 1 1987, 3, 639. (c) Aissaoui, H.; Boss, C.; Gude, M.; Koberstein, R.; Lehmann, D.; Sifferlen, T.; Trachsel, D. WO Patent 2009016560A2.

  14. (a) Gazieva, G. A.; Kravchenko, A. N. J. Heterocycl. Chem. 2015, 52, 1858. (b) Sigachev, A. S.; Kravchenko, A. N.; Lyssenko, K. A.; Belyakov, P. A.; Lebedev, O. V.; Makhova, N. N. Mendeleev Commun. 2003, 13, 190. (c) Gazieva, G. A.; Karpova, T. B.; Nechaeva, T. V.; Nelyubina, Yu. V.; Zanin, I. E.; Kravchenko, A. N. Synlett 2017, 858. (d) Gazieva, G. A.; Vasilevskii, S. V.; Belyakov, P. A.; Nelyubina, Yu. V.; Lubuzh, E. D.; Kravchenko, A. N. Mendeleev Commun. 2010, 20, 285.

  15. Bruker. APEX-III; Bruker AXS Inc.: Madison, 2019.

  16. Krause, L.; Herbst-Irmer, R.; Sheldrick, G. M.; Stalke, D. J. Appl. Crystallogr. 2015, 48, 3.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Adv. 2015, A71, 3.

  18. Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.

Download references

This study was financially supported by the Grants Council of the President of the Russian Federation for the State support of young Russian scientists (project MK-2375.2022.1.3).

The X-ray structural analysis and registration of highresolution mass spectra were performed at the Department of Structural Research of N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences (Moscow).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Galina А. Gazieva.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(10), 524–530

Supplementary Information

ESM 1

(PDF 3682 kb)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Vinogradov, D.B., Izmest’ev, A.N., Kravchenko, A.N. et al. A regioselective synthesis of imidazothiazolotriazines based on the cyclization of imidazotriazinethiones with phenacyl bromides. Chem Heterocycl Comp 58, 524–530 (2022). https://doi.org/10.1007/s10593-022-03123-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-022-03123-5

Keywords

Navigation