Skip to main content
Log in

Synthesis of 3-hydroxy-1H-pyrroles and pyridazines with a sterically hindered phenol moiety

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Novel pyrroles and pyridazines were obtained by the reaction of (4-hydroxy-3,5-di-tert-butylphenyl)glyoxal with 1,3-diketones and ammonium acetate or hydrazine hydrate. The study of antioxidant activity of the synthesized compounds using ABTS and PFRAP tests showed that 7-thoxo-7,8-dihydropyrimido[4,5-c]pyridazin-5(6H)-one has the highest activity.

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.

Similar content being viewed by others

References

  1. M. Rosini, E. Simoni, A. Milelli, A. Minarini, C. Melchiorre, J. Med. Chem., 2014, 57, 2821; DOI: https://doi.org/10.1021/jm400970m.

    Article  CAS  PubMed  Google Scholar 

  2. V. K. Koltover, Russ. Chem. Bull., 2010, 59, 37; DOI: https://doi.org/10.1007/s11172-010-0042-2.

    Article  CAS  Google Scholar 

  3. W. A. Yehye, N. A. Rahman, A. Ariffin, S. B. Abd Hamid, A. A. Alhadi, F. A. Kadir, M. Yaeghoobi, Eur. J. Med. Chem., 2015, 101, 295; DOI: https://doi.org/10.1016/j.ejmech.2015.06.026.

    Article  CAS  PubMed  Google Scholar 

  4. V. I. Latyuk, V. I. Kelarev, V. N. Koshelev, K. D. Korenev, Chem. Technol. Fuels and Oils (Engl. Transl.), 2002, 38, 312; DOI: https://doi.org/10.1023/A:1021282614918.

    Article  CAS  Google Scholar 

  5. V. N. Koshelev, V. I. Kelarev, N. V. Belov, O. V. Malova, S. L. Osipov, V. G. Spirkin, Chem. Technol. Fuels and Oils (Engl. Transl.), 1995, 31, 26; DOI: https://doi.org/10.1007/BF00727660.

    Article  Google Scholar 

  6. K. I. Kobrakov, V. I. Kelarev, E. V. Chernoglazova, V. M. Abu-Ammar, S. V. Gres’ko, Fibre Chem., 2003, 35, 429; DOI: https://doi.org/10.1023/B:FICH.0000020772.72219.b3.

    Article  CAS  Google Scholar 

  7. V. N. Koshelev, O. V. Primerova, A. S. Stupnikova, Butler. Soobsch. [Butler. Rep.], 2021, 67, 47; DOI: https://doi.org/10.37952/ROI-jbc-01/21-67-8-47 (in Russian).

    Google Scholar 

  8. D. K. Parker, Process for Preparing Hindered Alkenyl Phenols. Patent US 4072724A, 7 February 1978.

  9. H. A. Riley, A. R. Gray, Org. Synth., 1935, 15, 67; DOI: https://doi.org/10.15227/orgsyn.015.0067.

    Article  Google Scholar 

  10. N. O. Saldabol, J. Popelis, V Slavinska, Chem. Heterocycl. Compd., 2002, 38, 783; DOI: https://doi.org/10.1023/A:1020669301326.

    Article  CAS  Google Scholar 

  11. K. C. Joshi, V. N. Pathak, M. K. Goyal, J. Heterocycl. Chem., 1981, 18, 1651; DOI: https://doi.org/10.1002/jhet.5570180836.

    Article  CAS  Google Scholar 

  12. N. Kornblum, J. W. Powers, G. J. Anderson, W. J. Jones, H. O. Larson, O. Levand, W. M. Weaver, J. Am. Chem. Soc., 1957, 79, 6562; DOI: https://doi.org/10.1021/ja01581a057.

    Article  CAS  Google Scholar 

  13. S. S. Gholap, Eur. J. Med. Chem., 2016, 110, 13; DOI: https://doi.org/10.1016/j.ejmech.2015.12.017.

    Article  CAS  PubMed  Google Scholar 

  14. H. Fan, J. Peng, M. T. Hamann, J. F. Hu, Chem. Rev., 2008, 108, 264; DOI: https://doi.org/10.1021/cr078199m.

    Article  CAS  PubMed  Google Scholar 

  15. N. Singh, S. Singh, S. Kohli, A. Singh, H. Asiki, G. Rathee, R. Chandra, E. A. Anderson, Org. Chem. Front., 2021, 8, 5550; DOI: https://doi.org/10.1039/D0QO01574A.

    Article  CAS  Google Scholar 

  16. A. Kunfermann, M. Witschel, B. Illarionov, R. Martin, M. Rottmann, H. W. Höffken, M. Seet, W. Eisenreich, H. J. Knölker, M. Fischer, A. Bacher, Angew. Chem., Int. Ed., 2014, 53, 2235; DOI: https://doi.org/10.1002/anie.201309557.

    Article  CAS  Google Scholar 

  17. A. S. Demir, I. M. Akhmedov, Ö. Sesenoglu, Tetrahedron, 2002, 58, 9793; DOI: https://doi.org/10.1016/S0040-4020(02)01298-X.

    Article  CAS  Google Scholar 

  18. B. Khalili, P. Jajarmi, B. Eftekhari-Sis, M. M. Hashemi, J. Org. Chem., 2008, 73, 2090; DOI: https://doi.org/10.1021/jo702385n.

    Article  CAS  PubMed  Google Scholar 

  19. Z. X. He, Y. P. Gong, X. Zhang, L. Y. Ma, W. Zhao, Eur. J. Med. Chem., 2021, 209, 112946; DOI: https://doi.org/10.1016/j.ejmech.2020.112946.

    Article  CAS  PubMed  Google Scholar 

  20. M. Y. Jaballah, R. T. Serya, K. Abouzid, Drug Res., 2017, 67, 138; DOI: https://doi.org/10.1055/s-0042-119992.

    Article  CAS  Google Scholar 

  21. C. Altomare, S. Cellamare, L. Summo, M. Catto, A. Carotti, U. Thull, P. A. Carrupt, B. Testa, H. Stoeckli-Evans, J. Med. Chem., 1998, 41, 3812; DOI: https://doi.org/10.1021/jm981005y.

    Article  CAS  PubMed  Google Scholar 

  22. M. Rimaz, J. Khalafy, Arkivoc, 2010, 2, 110; DOI: https://doi.org/10.3998/ark.5550190.0011.208.

    Google Scholar 

  23. M. Rimaz, J. Khalafy, N. N. Pesyan, R. H. Prager, Aust. J. Chem., 2010, 63, 507; DOI: https://doi.org/10.1071/CH09569.

    Article  CAS  Google Scholar 

  24. J. Khalafy, M. Rimaz, L. Panahi, H. Rabiei, Bull. Korean Chem. Soc., 2011, 32, 2428; DOI: https://doi.org/10.5012/bkcs.2011.32.7.2428.

    Article  CAS  Google Scholar 

  25. M. A. Polovinkina, A. D. Osipova, V. P. Osipova, N. T. Berberova, D. B. Shpakovsky, Y. A. Gracheva, E. R. Milaeva, Russ. Chem. Bull., 2022, 71, 2218; DOI: https://doi.org/10.1007/s11172-022-3648-2.

    Article  CAS  Google Scholar 

  26. M. B. Arnao, A. Cano, M. Acosta, Food Chem., 2001, 73, 239; DOI: https://doi.org/10.1016/S0308-8146(00)00324-1.

    Article  CAS  Google Scholar 

  27. W. Thorwart, U. Gebert, R. Schleyerbach, R. R. Bartlett, 5-(3-Alkyl-5-tert-Butyl-4-Hydroxyphenyl)-2-Amino-6H-1,3,4-Thiadiazines, Patent US 4940790 A, 10 July 1990.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to K. V. Ilkov.

Ethics declarations

The authors declare no competing interests.

Additional information

No human or animal subjects were used in this research.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 9, pp. 2119–2124, September, 2023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ilkov, K.V., Gladkikh, A.A. & Koshelev, V.N. Synthesis of 3-hydroxy-1H-pyrroles and pyridazines with a sterically hindered phenol moiety. Russ Chem Bull 72, 2119–2124 (2023). https://doi.org/10.1007/s11172-023-4006-8

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-4006-8

Key words

Navigation