Skip to main content

Advertisement

SpringerLink
Log in

Effect of the nature of a fluorinated substituent on the synthesis of functionalized 1,3-diketones

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

Abstract

The synthesis of alkali metal and copper(ii) 1-polyfluoroalkyl-4,4-dimethoxypentane-1,3-dionates is reported. The subsequent treatment of these compounds with oxalic acid or ethylenediaminetetraacetic acid disodium salt affords functionalized 1,3-diketones. The nature of the polyfluoroalkyl substituent was found to affect the conditions of the Claisen condensation and the stability of the acetal group in acidic medium.

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

Similar content being viewed by others

References

  1. V. P. Ananikov, D. B. Eremin, S. A. Yakukhnov, A. D. Dilman, V. V. Levin, M. P. Egorov, S. S. Karlov, L. M. Kustov, A. L. Tarasov, A. A. Greish, A. A. Shesterkina, A. M. Sakharov, Z. N. Nysenko, A. B. Sheremetev, A. Yu. Stakheev, I. S. Mashkovsky, A. Yu. Sukhorukov, S. L. Ioffe, A. O. Terent’ev, V. A. Vil’, Y. V. Tomilov, R. A. Novikov, S. G. Zlotin, A. S. Kucherenko, N. E. Ustyuzhanina, V. B. Krylov, Y. E. Tsvetkov, M. L. Gening, N. E. Nifantiev, Mendeleev. Commun., 2017, 27, 425.

    Article  CAS  Google Scholar 

  2. B. Jeffries, Z. Wang, J. Graton, S. D. Holland, T. Brind, R. D. R. Greenwood, J.-Y. Questel, J. S. Scott, E. Chiarparin, B. Linclau, J. Med. Chem., 2018, 61, 10602.

    Article  CAS  Google Scholar 

  3. L. V. Politanskaya, G. A. Selivanova, E. V. Panteleeva, E. V. Tretyakov, V. E. Platonov, P. V. Nikul’shin, A. S. Vinogradov, Y. V. Zonov, V. M. Karpov, T. V. Mezhenkova, A. V. Vasilyev, A. B. Koldobskii, O. S. Shilova, S. M. Morozova, Ya. V. Burgart, E. V. Shchegolkov, V. I. Saloutin, V. B. Sokolov, A. Yu. Aksinenko, V. G. Nenajdenko, M. Yu. Moskalik, V. V. Astakhova, B. A. Shainyan, A. A. Tabolin, S. L. Ioffe, V. M. Muzalevskiy, E. S. Balenkova, A. V. Shastin, A. A. Tyutyunov, V. E. Boiko, S. M. Igumnov, A. D. Dilman, N. Yu. Adonin, V. V. Bardin, S. M. Masoud, D. V. Vorobyeva, S. N. Osipov, E. V. Nosova, G. N. Lipunova, V. N. Charushin, D. O. Prima, A. G. Makarov, A. V. Zibarev, B. A. Trofimov, L. N. Sobenina, K. V. Belyaeva, V. Ya. Sosnovskikh, D. L. Obydennov, S. A. Usachev, Russ. Chem. Rev., 2019, 88, 425; https://doi.org/10.1070/RCR4871.

    Article  CAS  Google Scholar 

  4. S. Mishra, S. Daniele, Chem. Rev., 2015, 115, 8379.

    Article  CAS  Google Scholar 

  5. G. F. Makhaeva, E. V. Rudakova, N. V. Kovaleva, S. V. Lushchekina, N. P. Boltneva, A. N. Proshin, E. V. Shchegolkov, Ya.V. Burgart, V. I. Saloutin, Russ. Chem. Bull., 2019, 68, 967; DOI: https://doi.org/10.1007/s11172-019-2507-2.

    Article  CAS  Google Scholar 

  6. L. S. Vasil’ev, S. V. Baranin, A. S. Dmitrenok, I. V. Zavarzin, Russ. Chem. Bull., 2019, 1795; DOI: https://doi.org/10.1007/s11172-019-2627-8.

  7. N. A. Artiukhova, G. V. Romanenko, G. A. Letyagin, A. S. Bogomyakov, S. E. Tolstikov, V. I. Ovcharenko, Russ. Chem. Bull., 2019, 68, 732; DOI: https://doi.org/10.1007/s11172-019-2480-9.

    Article  CAS  Google Scholar 

  8. V. B. Sokolov, A. Yu. Aksinenko, T. V. Goreva, T. A. Epishina, S. O. Bachurin, Russ. Chem. Bull., 2019, 68, 2241; DOI: https://doi.org/10.1007/s11172-019-2693-y.

    Article  CAS  Google Scholar 

  9. T. P. Vasilyeva, D. V. Vorobyeva, Russ. Chem. Bull., 2020, 69, 300; DOI: https://doi.org/10.1007/s11172-020-2760-4.

    Article  CAS  Google Scholar 

  10. M. V. Goryaeva, S. O. Kushch, Y. V. Burgart, V. I. Saloutin, Russ. Chem. Bull., 2020, 2163; DOI: https://doi.org/10.1007/s11172-020-3016-z.

  11. Yu. S. Kudyakova, D. N. Bazhin, M. V. Goryaeva, Ya. V. Burgart, V. I. Saloutin, Russ. Chem. Rev., 2014, 83, 120.

    Article  Google Scholar 

  12. E. V. Shchegol’kov, Y. V. Burgart, O. G. Khudina, V. I. Saloutin, O. N. Chupakhin, Russ. Chem. Rev., 2010, 79, 31.

    Article  Google Scholar 

  13. D. N. Bazhin, Yu. S. Kudyakova, G.-V. Roeschenthaler, Y. V. Burgart, P. A. Slepukhin, M. L. Isenov, V. I. Saloutin, V. N. Charushin, Eur. J. Org. Chem., 2015, 6306.

  14. D. N. Bazhin, Y. S. Kudyakova, A. Y. Onoprienko, P. A. Slepukhin, Y. V. Burgart, V. I. Saloutin, Chem. Heterocycl. Compd., 2017, 53, 1324; DOI: https://doi.org/10.1007/s10593-018-2214-1.

    Article  CAS  Google Scholar 

  15. D. N. Bazhin, Yu. S. Kudyakova, P. A. Slepukhin, Ya. V. Burgart, N. M. Malysheva, A. N. Kozitsina, A. V. Ivanova, A. S. Bogomyakov, V. I. Saloutin, Mendeleev. Commun., 2018, 28, 202.

    Article  CAS  Google Scholar 

  16. Yu. S. Kudyakova, A. Y. Onoprienko, P. A. Slepukhin, Y. V. Burgart, V. I. Saloutin, D. N. Bazhin, Chem. Heterocycl. Compd., 2019, 55, 517; DOI: https://doi.org/10.1007/s10593-019-02488-4.

    Article  CAS  Google Scholar 

  17. Yu. S. Kudyakova, D. N. Bazhin, P. A. Slepukhin, Y. V. Burgart, V. I. Saloutin, V. N. Charushin, Tetrahedron Lett., 2017, 58, 744.

    Article  CAS  Google Scholar 

  18. D. N. Bazhin, Yu. S. Kudyakova, N. A. Nemytova, Y. V. Burgart, V. I. Saloutin, J. Fluor. Chem., 2016, 186, 28.

    Article  CAS  Google Scholar 

  19. M. V. Goryaeva, Y. V. Burgart, Y. S. Kudyakova, M. A. Ezhikova, M. I. Kodess, P. A. Slepukhin, V. I. Saloutin, Eur. J. Org. Chem., 2015, 6306.

  20. P. A. Slepukhin, N. S. Boltacheva, V. I. Filyakova, V. N. Charushin, Russ. Chem. Bull., 2019, 68, 1213; DOI: https://doi.org/10.1007/s11172-019-2543-y.

    Article  CAS  Google Scholar 

  21. D. N. Bazhin, Yu. S. Kudyakova, Y. V. Burgart, V. I. Saloutin, Tetrahedron Lett., 2012, 53, 1961.

    Article  CAS  Google Scholar 

  22. J. Han, A. M. Remete, L. S. Dobson, L. Kiss, K. Izawa, H. Moriwaki, V. A. Soloshonok, D. O’Hagan, J. Fluor. Chem., 2020, 239, 109639.

    Article  CAS  Google Scholar 

  23. A. V. Safrygin, R. A. Irgashev, P. A. Slepukhin, G.-V. Röschenthaler, V. Y. Sosnovskikh, Tetrahedron, 2015, 71, 8535.

    Article  CAS  Google Scholar 

  24. M. Grünebaum, A. Buchheit, C. Günther, H.-D. Wiemhöfer, Tetrahedron Lett., 2016, 57, 1555.

    Article  Google Scholar 

  25. D. E. Pugachyov, T. S. Kostryukova, N. P. Ivanovskaya, A. I. Lyamin, D. V. Romanov, S. V. Moiseyev, G. V. Zatonskii, N. S. Osin, N. V. Vasilyev, Russ. J. Gen. Chem., 2019, 89, 96; DOI: https://doi.org/10.1134/S1070363219050165.

    Article  Google Scholar 

  26. T. Zhang, J. Pan, J. Duan, J. Wu, W. Zhang, F. Wu, ChemCatChem, 2019, 11, 5778.

    Article  CAS  Google Scholar 

  27. D. N. Bazhin, D. L. Chizhov, G.-V. Röschenthaler, Y. S. Kudyakova, Y. V. Burgart, P. A. Slepukhin, V. I. Saloutin, V. N. Charushin, Tetrahedron Lett., 2014, 55, 5714.

    Article  CAS  Google Scholar 

  28. D. N. Bazhin, Y. S. Kudyakova, Y. V. Burgart, V. I. Saloutin, Russ. Chem. Bull., 2018, 68, 497; DOI: https://doi.org/10.1007/s11172-018-2099-2.

    Article  Google Scholar 

  29. D. L. Chizhov, D. V. Belyaev, D. S. Yachevskii, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin, J. Fluor. Chem., 2017, 199, 39.

    Article  CAS  Google Scholar 

  30. S. Büttner, W. Desens, D. Michalik, P. Langer, Eur. J. Org. Chem., 2011, 6663.

  31. V. V. Krisyuk, S. U. Kyzy, T. V. Rybalova, I. A. Baidina, I. V. Korolkov, D. L. Chizhov, D. N. Bazhin, Y. S. Kudyakova, J. Coord. Chem., 2018, 71, 2194.

    Article  CAS  Google Scholar 

  32. D. N. Bazhin, Yu. S. Kudyakova, A. S. Bogomyakov, P. A. Slepukhin, G. A. Kim, Ya. V. Burgart, V. I. Saloutin, Inorg. Chem. Front., 2019, 6, 40.

    Article  CAS  Google Scholar 

  33. Y. S. Kudyakova, P. A. Slepukhin, M. S. Valova, Y. V. Burgart, V. I. Saloutin, D. N. Bazhin, Russ. J. Coord. Chem., 2020, 46, 485; DOI: https://doi.org/10.31857/S0132344X20070026.

    Article  Google Scholar 

  34. Y. S. Kudyakova, P. A. Slepukhin, M. S. Valova, Y. V. Burgart, V. I. Saloutin, D. N. Bazhin, Eur. J. Inorg. Chem., 2020, 523.

  35. Y. S. Kudyakova, P. A. Slepukhin, M. S. Valova, Y. V. Burgart, V. I. Saloutin, D. N. Bazhin, J. Mol. Struct., 2021, 1226, 129331.

    Article  CAS  Google Scholar 

  36. U. Berens, D. Leckel, S. C. Oepen, J. Org. Chem., 1995, 60, 8204.

    Article  CAS  Google Scholar 

  37. O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Cryst., 2009, 42, 339.

    Article  CAS  Google Scholar 

  38. G. M. Sheldrick, Acta Cryst., 2008, A64, 112.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620108, Yekaterinburg, Russian Federation

    Yu. S. Kudyakova, A. Ya. Onoprienko, Yu. O. Edilova, Ya. V. Burgart, V. I. Saloutin & D. N. Bazhin

  2. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 ul. Mira, 620002, Yekaterinburg, Russian Federation

    A. Ya. Onoprienko, Yu. O. Edilova, Ya. V. Burgart, V. I. Saloutin & D. N. Bazhin

Authors
  1. Yu. S. Kudyakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. Ya. Onoprienko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. O. Edilova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ya. V. Burgart
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. I. Saloutin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. D. N. Bazhin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to D. N. Bazhin.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 745–752, April, 2021.

This work was financially supported by the Russian Science Foundation (Project No. 19-73-00242).

The X-ray diff raction and physicochemical studies of the complexes were performed using facilities of the Joint Use Center “Spectroscopy and Analysis of Organic Compounds” (JUC SAOC) of the I. Ya. Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences.

No human or animal subjects were involved in this research.

The authors declare no conflict of interest, financial or otherwise.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kudyakova, Y.S., Onoprienko, A.Y., Edilova, Y.O. et al. Effect of the nature of a fluorinated substituent on the synthesis of functionalized 1,3-diketones. Russ Chem Bull 70, 745–752 (2021). https://doi.org/10.1007/s11172-021-3145-z

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-021-3145-z

Key words

Search

Navigation