Skip to main content
Log in

1-Allyl- and 1-(2-Bromopropyl)-2-amino-3-carboxy(carbalkoxy)methylbenzimidazolium Quaternary Salts in the Synthesis of Imidazo[1,2-a]benzimidazole Derivatives

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

Abstract

1-Allyl(2-bromopropyl)-3-carboxy(carbalkoxy)methyl-2-aminobenzimidazolium halides and their 2-iminobenzimidazoline forms were synthesized. Their cyclization into functionalized imidazo[1,2-a]benzimidazole derivatives was studied. Some further transformations of obtained imidazobenzimidazoles with the participation of reactive substituents and an activated methylene group were studied.

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.

Scheme
Scheme
Scheme
Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Gravel, J. and Schmitzer, A.R., Org. Biomol. Chem., 2017, vol. 15, p. 1051. https://doi.org/10.1039/C6OB02293F

    Article  CAS  PubMed  Google Scholar 

  2. Sangeeta, G.P.V., Purna, N.K., Risy, N.J., Murali, M., and Kumarn, K., Microb. Pathogen, 2018, vol. 124, p. 258. https://doi.org/10.1016/j.micpath.2018.08.046

    Article  CAS  Google Scholar 

  3. Zarubaev, V.V., Morkovnik, A.S., Divaeva, L.N., Karpinskaya, L.A., and Borodkin, G.S., Bioorg. Med. Chem., 2016, vol. 24, p. 5796. https://doi.org/10.1016/j.bmc.2016.09.036

    Article  CAS  PubMed  Google Scholar 

  4. Shelton, K.L., DeBord, M.A., Wagers, P.O., Southerland, M.R., Williams, T.M., Robishaw, N.K., Shriver, L.P., Tessier, C.A., Panzner, M.J., and Youngs, W.J., Bioorg. Med. Chem., 2017, vol. 25, p. 421. https://doi.org/10.1016/j.bmc.2016.11.009

    Article  CAS  PubMed  Google Scholar 

  5. Yigit, M., Yigit, B., Taslimi, P., Ozdemir, I., Karaman, M., and Gulçin, L., J. Mol. Struct., 2020, vol. 1207, p. 127802. https://doi.org/10.1016/j.molstruct.2020.127802

    Article  Google Scholar 

  6. Spasov, A.A, Kucheryavenko, A.F., Gaidukova, K.A., Kosolapov, V A., and Zhukovskayа, O.N., Res. Results Pharmacol., 2020, vol. 6, no. 1, p. 1. https://doi.org/10.3897/rrpharmacology.6.503732

    Article  CAS  Google Scholar 

  7. Spasov, A.A., Zhukovskaya, O.N., Babkov, D.A., Brigadirova, A.A., Babkova, V.A., Morkovnik, A.S., Litvinov, R.A., and Sokolova, E.V., Russ. Chem. Bull., 2020, vol. 4, p. 774. https://doi.org/10.1007/s11172-020-2832-5

    Article  CAS  Google Scholar 

  8. RF Patent 2623439, 2017.

  9. RF Patent 2526902, 2014.

  10. RF Patent 2386634C2, 2010.

  11. Anisimova, V.A. and Tolpygin, I.E., Russ. J. Org. Chem., 2011, vol. 47, p. 1346. https://doi.org/10.1134/S1070428011090156

    Article  CAS  Google Scholar 

  12. Simonov, A.M., Anisimova, V.A., and Borisova, T.A., Chem. Heterocycl. Compd., 1973, vol. 9, p. 99. https://doi.org/10.1007/BF00476162

    Article  Google Scholar 

  13. Anisimova, V.A., Kuz’menko, T.A., Spasov, A.A., Bocharova, I.A., and Orobinskaya, T.A., Pharm. Chem. J., 1999, vol. 33, p. 361.

    Article  CAS  Google Scholar 

  14. Descours, D. and Festa, D., Synthesis, 1983, vol. 12, p. 1033. https://doi.org/10.1055/s-1983-30617

    Article  Google Scholar 

  15. Mobinikhaledi, A., Foroughifar, N., Kalhor, M., and Mirabolfathy, M., J. Heterocycl. Chem., 2010, vol. 47, p. 77. https://doi.org/10.1002/jhet.264

    Article  CAS  Google Scholar 

  16. Riyadh, S.M., Farghaly, T.A., and Gomha, S.M., Arch. Pharm. Res., 2010, vol. 33, p. 1721. https://doi.org/10.1007/s12272-010-1102-8

    Article  CAS  PubMed  Google Scholar 

  17. ElKalyoubi, S.A., Chem. Central J., 2018, vol. 12, Article 64. https://doi.org/10.1186/s1306501804243

  18. Anisimova, V.A., Simonov, A.M., and Pozharskii, A.F., Chem. Heterocycl. Compd., 1973, vol. 9, p. 731. https://doi.org/10.1007/BF00472318

    Article  Google Scholar 

  19. Karrouchi, K., Radi, S., Ramli, Y., Taoufik, J., Mabkhot, Y.N., Al-aizari, F.A., and Ansar, M., Molecules, 2018, vol. 23, no. 1, p. 134. https://doi.org/10.3390/molecules23010134

    Article  CAS  PubMed Central  Google Scholar 

  20. Rizk, S.A., El-Sayed, A.A., and Mounier, M.M., J. Heterocycl. Chem., 2017, vol. 54, p. 3358. https://doi.org/10.1002/jhet.2956

    Article  CAS  Google Scholar 

  21. El-Sehemi, A.G., Bondock, S., and Ammar, Y.A., Med. Chem. Res., 2014, vol. 23, p. 827. https://doi.org/10.1007/s00044-013-0650-0

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

This work was carried out using the equipment of the Center for Collective Use of the Southern Federal University.

Funding

This work was financially supported by the Ministry of Science and Higher Education of the Russian Federation (State assignment in the field of scientific activity, Southern Federal University, 2020, project FENW-2020-0031 (0852-2020-0031)).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. S. Morkovnik.

Ethics declarations

No conflict of interest was declared by the authors.

Additional information

Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 7, pp. 998–1009 https://doi.org/10.31857/S0044460X21070039.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhukovskaya, O.N., Morkovnik, A.S. & Borodkin, G.S. 1-Allyl- and 1-(2-Bromopropyl)-2-amino-3-carboxy(carbalkoxy)methylbenzimidazolium Quaternary Salts in the Synthesis of Imidazo[1,2-a]benzimidazole Derivatives. Russ J Gen Chem 91, 1271–1281 (2021). https://doi.org/10.1134/S1070363221070033

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363221070033

Keywords:

Navigation