Skip to main content
Log in

Halogenation and nitration of 1-carboxymethyl-5-methyluracil. Halophilic reaction involving acetic anhydride

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

Abstract

1-Carboxymethyl-5-halo-6-hydroxy-5-methyl-5,6-dihydrouracils and 1-carboxymethyl-6-hydroxy-5-methyl-5-mtro-5,6-dihydrouracils were synthesized for the first time by oxidative halogenation and nitration of 1-carboxymethyl-5-methyluracil. Dihydrouracil derivatives bearing a Br atom at position C(5) and a hydroxy group at position C(6) treated with Ac2O undergo deoxyhalogenation.

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.

Institutional subscriptions

Similar content being viewed by others

References

  1. M. S. Novikov, A. N. Geisman, Chem. Heterocycl. Compd., 2014, 49, 1426; DOI: https://doi.org/10.1007/s10593-014-1394-6.

    Article  CAS  Google Scholar 

  2. I. B. Chernikova, S. L. Khursan, M. Yu. Eropkin, M. S. Yunusov, Pharm. Chem. J., 2019, 53, 108; DOI: https://doi.org/10.1007/s11094-019-01962-9.

    Article  CAS  Google Scholar 

  3. D.-Z. Li, Q.-Z. Zhang, C.-Y. Wang, Y.-L. Zhang, X.-Y. Li, J.-T. Huang, H.-Y. Liu, Zh.-D. Fu, H.-X. Song, J.-P. Lin, T.-F. Ji, X.-D. Pan, Eur. J. Med. Chem., 2017, 125, 1235; DOI: https://doi.org/10.1016/j.ejmech.2016.11.013.

    Article  CAS  Google Scholar 

  4. Yu. S. Zimin, N. S. Borisova, G. R. Timerbaeva, A. R. Gimadieva, A. G. Mustafin, Pharm. Chem. J., 2017, 50, 649; DOI: https://doi.org/10.1007/s11094-017-1507-5.

    Article  CAS  Google Scholar 

  5. L. Saikia, P. Roudragouda, As. J. Thakur, Bioorg. Med. Chem. Lett., 2016, 26, 992; DOI: https://doi.org/10.1016/j.bmcl.2015.12.047.

    Article  CAS  Google Scholar 

  6. A. R. Gimadieva, V. A. Myshkin, A. G. Mustafin, Yu. N. Chernyschenko, A. Kh. Fattakhov, I. B. Abdrakhmanov, G. A. Tolstikov, Dokl. Biol. Sci., 2013, 448, 7; DOI: https://doi.org/10.1134/S0012496613010110.

    Article  CAS  Google Scholar 

  7. M. E. Mercurio, S. Tomassi, M. Gaglione, R. Russo, A. Chambery, S. Lama, P. Stiuso, S. Cosconati, E. Novellino, S. Di Maro, A. Messere, J. Org. Chem., 2016, 81, 11612; DOI: https://doi.org/10.1021/acs.joc.6b01829.

    Article  CAS  Google Scholar 

  8. I. B. Chernikova, M. S. Yunusov, A. G. Mustaphin, Russ. Chem. Bull., 2020, 69, 114; DOI: https://doi.org/10.1007/s11172-020-2731-9.

    Article  CAS  Google Scholar 

  9. I. B. Chernikova, S. L. Khursan, L. V. Spirikhin, M. S. Yunusov, Russ. Chem. Bull., 2013, 62, 2445; DOI: https://doi.org/10.1007/s11172-013-0354-0.

    Article  CAS  Google Scholar 

  10. A. J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer, Berlin—Heidelberg, 1983, 149 pp.

    Book  Google Scholar 

  11. I. B. Chernikova, S. L. Khursan, L. V. Spirikhin, M. S. Yunusov, Chem. Heterocycl. Compd., 2015, 51, 568; DOI: https://doi.org/10.1007/s10593-015-1737-y.

    Article  CAS  Google Scholar 

  12. I. B. Chernikova, L. V. Spirikhin, M. F. Abdullin, M. S. Yunusov, Chem. Nat. Compd., 2017, 53, 1141; DOI: https://doi.org/10.1007/s10600-017-2218-6.

    Google Scholar 

  13. N. S. Zefirov, N. K. Chapovskaya, D. I. Makhon’kov, Zh. Org. Khim. [J. Org. Chem.], 1976, 12, 617 (in Russian).

    Google Scholar 

  14. N. S. Zefirov, D. I. Makhon’kov, Russ. Chem. Rev., 1980, 49, 637; DOI: https://doi.org/10.1070/RC1980v049n04ABEH002463.

    Article  CAS  Google Scholar 

  15. N. S. Zefirov, D. I. Makhon’kov, Chem. Rev., 1982, 82, 615; DOI: https://doi.org/10.1021/cr00052a004.

    Article  CAS  Google Scholar 

  16. G. S. Abdrakhimova, M. Yu. Ovchinnikov, A. N. Lobov, L. V. Spirikhin, S. P. Ivanov, S. L. Khursan, J. Phys. Org. Chem., 2014, 27, 876; DOI: https://doi.org/10.1002/poc.3350.

    Article  CAS  Google Scholar 

  17. V. G. Kasradze, I. B. Ignatyeva, R. A. Khusnutdinov, K. Yu. Suponitskii, M. Yu. Antipin, M. S. Yunusov, Chem. Heterocycl. Compd., 2012, 48, 1018; DOI: https://doi.org/10.1007/s10593-012-1094-z.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to I. B. Chernikova.

Additional information

The spectral part of the study was carried out on the equipment of the “Khimiya” User Service Center of the Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences.

This work was financially supported by the Ministry of Higher Education and Science of the Russian Federation (Topic No. AAAA-A20-120012090026-9).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2159—2162, November, 2020.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chernikova, I.B., Yunusov, M.S. Halogenation and nitration of 1-carboxymethyl-5-methyluracil. Halophilic reaction involving acetic anhydride. Russ Chem Bull 69, 2159–2162 (2020). https://doi.org/10.1007/s11172-020-3015-0

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-020-3015-0

Keywords

Navigation