Skip to main content
SpringerLink
Log in

Facile Synthesis of l-3,5-Diiodotyrosine by Solvent-Free Iodination of l-Tyrosine with 2,4,6,8-Tetraiodoglycoluril

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

Abstract

l-Tyrosine is readily iodinated by 2,4,6,8-tetraiodoglycoluril under solvent-free grinding in the presence of a catalytic amount of acetic acid to give l-3,5-diodothyrosine in high yield. The method is also applicable for diiodination of ortho- and para-nitrophenols.

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

REFERENCES

  1. Xua, X., Ge, R., Li, L., Wang, J., Lu, X., Xue, S., Chen, X., Li, Z., and Bian, J., Eur. J. Med. Chem., 2018, vol. 143, p. 1325. https://doi.org/10.1016/j.ejmech.2017.10.031

    Article  CAS  Google Scholar 

  2. Puratchikody, A., Umamaheswari, A., Irfan, N., Sinha, S., Manju, S.L., Ramanan, M., Ramamoorthy, G., and Doble, M., New J. Chem., 2019, vol. 43, p. 834. https://doi.org/10.1039/C8NJ04385J

    Article  CAS  Google Scholar 

  3. Fujita, N., Ono, Y., Sano, A., Kimata, M., Oyama, S., Hashimoto, K., Sato, I., Kudo, M., Miyashiro, Y., Fujikata, A., and Tanaka, Y., Eur. J. Endocrinology, 2022, vol. 186, p. 245. https://doi.org/10.1530/EJE-21-0901

    Article  CAS  Google Scholar 

  4. Yan, R., Li, Y., Müller, J., Zhang, Y., Singer, S., Xia, L., Zhong, X., Gertsch, J., and Altmann, K.-H., Cell Discovery, 2021, vol. 7, p. 16. https://doi.org/10.1038/s41421-021-00247-4

    Article  CAS  Google Scholar 

  5. Mourier, G., Moroder, L., and Previero, A., Z. Naturforsch. B, 1984, vol. 39, p. 101. https://doi.org/10.1515/znb-1984-0119

    Article  Google Scholar 

  6. Roy, G., Nethajia, M., and Mugesh, G., Org. Biomol. Chem., 2006, vol. 4, p. 2883. https://doi.org/10.1039/B604060H

    Article  CAS  Google Scholar 

  7. Chaikovski, V.K., Filimonov, V.D., Yagovkin, A.Yu., and Kharlova, T.S., Tetrahedron Lett., 2000, vol. 41, p. 9101. https://doi.org/10.1016/S0040-4039(00)01624-5

    Article  CAS  Google Scholar 

  8. Chaikovskii, V.K., Funk, A.A., Filimonov, V.D., Petrenko, T.V., and Kets, T.S., Russ. J. Org. Chem., 2008, vol. 44, p. 935. https://doi.org/10.1134/S1070428008060286

    Article  CAS  Google Scholar 

  9. Chaikovski, V.K., Filimonov, V.D., Yagovkin, A.Yu, and Ogorodnikov, V.D., Russ. Chem. Bull., 2001, vol. 50, p. 2411. https://doi.org/10.1023/A:1015047916151

    Article  CAS  Google Scholar 

  10. Sharma, V., Srivastava, P., Bhardwaj, S.K., and Agarwal, D.D., Green Process. Synth., 2018, vol. 7, p. 477. https://doi.org/10.1515/gps-2017-0072

    Article  CAS  Google Scholar 

  11. Krasnokutskaya, E.A., Trusova, M.E., and Filimonov, V.D., Russ. J. Org. Chem., 2005, vol. 41, p. 1750. https://doi.org/10.1007/s11178-006-0031-y

    Article  CAS  Google Scholar 

  12. Filimonov, V.D., Krasnokutskaya, E.A., Poleshchuk, O.Kh., Lesina, Yu.A., and Chaikovskii, V.K., Russ. Chem. Bull., 2006, vol. 55, p. 1328. https://doi.org/10.1007/s11172-006-0422-9

    Article  CAS  Google Scholar 

  13. Wingard, L.A., Johnson, E.C., and Sabatini, J.J., Tetrahedron Lett., 2016, vol. 57, p. 1681. https://doi.org/10.1016/j.tetlet.2016.03.013

    Article  CAS  Google Scholar 

  14. Kiran, Y.B., Konakahara, T., and Sakai, N., Synthesis, 2008, p. 2327. https://doi.org/10.1055/s-2008-1078598

Download references

Funding

This research was funded by the Ministry of Education and Science through the Nauka program (project no. FSWW-2020-011).

Author information

Authors and Affiliations

  1. Siberian State Medical University, 634050, Tomsk, Russia

    I. L. Filimonova

  2. National Research Tomsk Polytechnic University, 634050, Tomsk, Russia

    E. A. Krasnokutskaya, E. V. Khovrenko & E. A. Pakhomov

Authors
  1. I. L. Filimonova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. A. Krasnokutskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. V. Khovrenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. A. Pakhomov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. L. Filimonova.

Ethics declarations

The authors declare no conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 11, pp. 1259–1262 https://doi.org/10.31857/S0514749222110180.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Filimonova, I.L., Krasnokutskaya, E.A., Khovrenko, E.V. et al. Facile Synthesis of l-3,5-Diiodotyrosine by Solvent-Free Iodination of l-Tyrosine with 2,4,6,8-Tetraiodoglycoluril. Russ J Org Chem 58, 1673–1675 (2022). https://doi.org/10.1134/S1070428022110197

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428022110197

Keywords:

Search

Navigation