Skip to main content
SpringerLink
Log in

First Examples of Phosphoric Anhydride-Promoted O- and N-Acylation

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

Abstract

It was shown that phosphoric anhydride can be used for the synthesis of esters and amides of carboxylic acids when they react with compounds containing hydroxy ord primary amino groups. A new method for preparation of paracetamol was proposed for obtaining paracetamol. An example of the reverse reactivity of these nucleophilic centers in para-aminophenol molecule was revealed.

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
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme

REFERENCES

  1. Perechen’ prekursorov and neobkhodimykh khimikatov, kotoryye obychno ispol'zuyutsya dlya nelegal'nogo proizvodstva nekotorykh podlezhashchikh kontrolyu veshchestv (List of precursors and chemicals commonly used in the illegal production of certain controlled substances). https://www.consultant.ru/document/cons_doc_LAW_283828/ce505a5244637b5dbb0cc62b4d7ad0ea121b5aad/?ysclid=llw6ow937l355247465

  2. Wang, Q. and Deng, Y., Patent CN102675080A, 2014.

  3. Shafran, Yu.M., Bakulev, V.A., Shevyrin, V.A., and Kolobov, M.Yu., Chem. Heterocycl. Compd., 1993, no. 11, p. 724. https://doi.org/10.1007/bf00531556

    Article  Google Scholar 

  4. Beliaev, N. and Shafran, Yu., Patent WO 2016038061Al, 2016.

  5. Micheli, R.A., Booth, A.N., Livingston, A.L., and Bickoff, E.M., J. Med. Pharm. Chem., 1962, vol. 5, p. 321. https://doi.org/10.1021/jm01237a010

    Article  CAS  PubMed  Google Scholar 

  6. Wessely, F. and Prillinger, F., Chem. Ber., 1939, vol. 72, p. 629.

    Article  Google Scholar 

  7. Marrian, G.F. and Haslewood, G.A.D., Biochem. J., 1932, vol. 26, p. 1227. https://doi.org/10.1042/bj0261227

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Ohta, H., Ishizaka, T., Tatsuzuki, M., Yoshinaga, M., Iida, I., Yamaguchi, T., Tomishima, Y., Futaki, N., Toda, Y., and Saito, S., Bioorg. Med. Chem., 2008, vol. 16, no. 3, p. 1111. https://doi.org/10.1016/j.bmc.2007.10.087

    Article  CAS  PubMed  Google Scholar 

  9. Chemical Note. https://chemicalnote.com/formic-acid-methanoic-acid-laboratory-preparation-properties-and-uses

  10. Jones, C.D., Luke, R.W.A, and Mccoull, W., Patent WO 2005060970, 2005.

  11. Medina-Ramos, W., Mojica, M.A., Cope, E.D., Hart, R.J., Pollet, P., Eckert, Ch.A., and Liotta, Ch.L., Green Chem., 2014, vol. 16, no. 4, p. 2147. https://doi.org/10.1039/c3gc42569j

    Article  CAS  Google Scholar 

  12. Yamamoto, T., Harigaya, Y., and Okawara, M., Tetrahedron, 1978, vol. 34, no. 20, p. 3097. https://doi.org/10.1016/0040-4020(78)87005-7

    Article  CAS  Google Scholar 

  13. Wang, Y., Liu, W.-J., Yin, L., Li, H., Chen, Z.-H., Zhu, D.-X., Song, X.-Q., Cheng, Z.-Z., Song, P., Wang, Z., and Li, Z.-G., Bioorg. Med. Chem. Lett., 2018, vol. 28, no. 5, p. 974. https://doi.org/10.1016/j.bmcl.2017.12.068

    Article  CAS  PubMed  Google Scholar 

  14. Kalyvas, V. and McIntyre, J.E., Mol. Cryst. Liq. Cryst., 1982, vol. 80, no. 1, p. 105. https://doi.org/10.1080/00268948208071024

    Article  CAS  Google Scholar 

  15. El-Gamal, M.I., Zaraei, S.O., Foster, P.A., Anbar, H.S., El-Gamal, R., El-Awady, R., and Potter, B.V.L., Bioorg. Med. Chem., 2020, vol. 28, no. 8, p. 115406. https://doi.org/10.1016/j.bmc.2020.115406

    Article  CAS  PubMed  Google Scholar 

  16. Sovak, M., Terry, R.C., Douglass, J.G., Bakir, F., Brown, J., and Cugley, P., Pat. WO2001008647 (2001).

  17. Bhardwaj, B., Nivrutti, A.A., Saraf, P., Shrivastava, S.K., Tripathi, M., Tripathi, P.N., Verma, A., and Waiker, D.K., J. Mol. Struct., 2022, vol. 1262. https://doi.org/10.1016/j.molstruc.2023.135517

  18. Xu, T. and Alper, H., J. Am. Chem. Soc., 2014, vol. 136, no. 49, p. 16970. https://doi.org/10.1021/ja508588b

    Article  CAS  PubMed  Google Scholar 

  19. Ikeda, S.-I., Kimura, U., Ashizawa, T., Gomi, K., Saito, H., Kasai, M., Kanazawa, J., Sasaki, K., Nukui, E., Okabe, M., and Sato, S., Pat. US 5952355A (1999). USA.

  20. Línzembold, I., Czett, D., Böddi, K., Kurtán, T., Király, S.B., Gulyás-Fekete, G., Takátsy, A., Lóránd, T., Deli, J., Agócs, A., and Nagy, V., Molecules, 2020, vol. 25, no. 3, p. 636. https://doi.org/10.3390/molecules25030636

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. Sowjanya, T., Jayaprakash Rao, Y., and Murthy, N.Y.S., Russ. J. Gen. Chem., 2017, vol. 87, no. 8, p. 1864. https://doi.org/10.1134/s1070363217080357

    Article  CAS  Google Scholar 

  22. Majumdar, S. and Sloan, K.B., Int. J. Pharm., 2007, vol. 337, nos. 1–2, p. 48. https://doi.org/10.1016/j.ijpharm.2006.12.026

    Article  CAS  PubMed  Google Scholar 

  23. Horner, L. and Steppan, H., Ann., 1957, vol. 606, p. 24.

    CAS  Google Scholar 

  24. Itoh, N., Sakamoto, T., Miyazawa, E., and Kikugawa, Y., J. Org. Chem., 2002, vol. 67, no. 21, p. 7424. https://doi.org/10.1021/jo0260847

    Article  PubMed  Google Scholar 

  25. Vickers, S., Triggle, D.J., and Garrison, D.R., J. Chem. Soc. (C), 1968, p. 632. https://doi.org/10.1039/J39680000632

Download references

Funding

This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.

Author information

Authors and Affiliations

  1. Institute of Chemical Engineering, Ural Federal University, 620002, Yekaterinburg, Russia

    Yu. M. Shafran & T. A. Pospelova

Authors
  1. Yu. M. Shafran
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. A. Pospelova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yu. M. Shafran.

Ethics declarations

The authors declare no conflict of interest.

Additional information

Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shafran, Y.M., Pospelova, T.A. First Examples of Phosphoric Anhydride-Promoted O- and N-Acylation. Russ J Gen Chem 93, 3021–3033 (2023). https://doi.org/10.1134/S1070363223120010

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363223120010

Keywords:

Search

Navigation