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Synthesis of New Diaryl(hetaryl)ethylphosphonic Acids

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Abstract

An original, new method for the synthesis of previously unknown diaryl(hetaryl)ethylphosphonic acids containing pharmacophoric fragments was developed as a result of the acid-catalyzed reaction of (2-ethoxyvinyl)phosphonic dichloride with heterocyclic compounds such as 4-hydroxy-6-methyl-2-pyrone, 4-hydroxycoumarin, and also thymol and carvacrol containing a hydroxyl group. Composition and structure of all diaryl(hetaryl)ethylphosphonic acids were confirmed according to 1H, 13С and 31P NMR, IR spectroscopy, mass spectrometry and elemental analysis data.

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REFERENCES

  1. Gazizov, A.S., Burilov, A.R., Pudovik, M.A., and Sinyashin, O.G., Russ. Chem. Rev., 2017, vol. 86, p. 75. https://doi.org/10.1070/RCR4622

    Article  CAS  Google Scholar 

  2. Smolobochkin, A.V., Gazizov, A.S., Burilov, A.R., Pudovik, M.A., and Sinyashin, O.G., Russ. Chem. Rev., 2019, vol. 88, p. 1104. https://doi.org/10.1070/RCR4891

    Article  CAS  Google Scholar 

  3. Kim, C., Jeong, S., Lee, H.W., Kim, Y.K., and Yoon, S.S., Mol. Cryst. Liq. Cryst., 2017, vol. 651, p. 9. https://doi.org/10.1080/15421406.2017.1338486

    Article  CAS  Google Scholar 

  4. Mao, G., Orita, A., Fenenko, L., Yahiro, M., Adachi, C., and Otera, J., Mater. Chem. Phys., 2009, vol. 115, p. 378. https://doi.org/10.1016/j.matchemphys.2008.12.015

    Article  CAS  Google Scholar 

  5. Chiang, C.-L., Shu, C.-F., and Chen, C.-T., Org. Lett., 2005, vol. 7, p. 3717. https://doi.org/10.1021/ol0513591

    Article  PubMed  CAS  Google Scholar 

  6. Motoyoshiya, J., Ikeda, T., Tsuboi, S., Kusaura, T., Takeuchi, Y., Hayashi, S., Yoshioka, S., Takaguchi, Y., and Aoyama, H., J. Org. Chem., 2003, vol. 68, p. 5950. https://doi.org/10.1021/jo030046l

    Article  PubMed  CAS  Google Scholar 

  7. Mucha, A., Kafarski, P., and Berlicki, Ł., J. Med. Chem., 2011, vol. 54, p. 5955. https://doi.org/10.1021/jm200587f

    Article  PubMed  CAS  Google Scholar 

  8. Baig, M.Z.K., Pallikonda, G., Trivedi, P., Tulichala, R.N.P., Ghosh, B., and Chakravarty, M., Chem. Select., 2016, vol. 1, p. 4332. https://doi.org/10.1002/slct.201600978

    Article  CAS  Google Scholar 

  9. Palchaudhuri, R., Nesterenko, V., and Hergenrother, P., J. Am. Chem. Soc., 2008, vol. 130, p. 10274. https://doi.org/10.1021/ja8020999

    Article  PubMed  CAS  Google Scholar 

  10. Horsman, G.P. and Zechel, D.L., Chem. Rev., 2017, vol. 117, p. 5704. https://doi.org/10.1021/acs.chemrev.6b00536

    Article  PubMed  CAS  Google Scholar 

  11. Demmer, C.S., Krogsgaard-Larsen, N., and Bunch, L., Chem. Rev., 2011, vol. 111, p. 7981. https://doi.org/10.1021/cr2002646

    Article  PubMed  CAS  Google Scholar 

  12. Rajeshwaran, G.G., Nandakumar, M., Sureshbabu, R., and Mohanakrishnan, A.K., Org. Lett., 2011, vol. 13, p. 1270. https://doi.org/10.1021/ol1029436

    Article  PubMed  CAS  Google Scholar 

  13. Huang, H. and Kang, J.Y., Org. Lett., 2017, vol. 19, p. 5988. https://doi.org/10.1021/acs.orglett.7b03019

    Article  PubMed  CAS  Google Scholar 

  14. Prasad, S.S., Singh, D.K., and Kim, I., J. Org. Chem., 2019, vol. 84, p. 6323. https://doi.org/10.1021/acs.joc.9b00668

    Article  PubMed  CAS  Google Scholar 

  15. Golitsin, S.M., Beletskaya, I.P., and Titanyuk, I.D., Synthesis, 2020, vol. 52, p. 775. https://doi.org/10.1055/s-0039-1690758

    Article  CAS  Google Scholar 

  16. Knyazeva, I.R., Burilov, A.R., Pudovik, M.A., and Habicher, W.D., Russ. Chem. Rev., 2013, vol. 82, p. 150. https://doi.org/10.1070/RC2013v082n02ABEH004296

    Article  CAS  Google Scholar 

  17. Sadykova, Yu.M., Knyazeva, I.R., Burilov, A.R., Pudovik, M.A., Dobrynin, A.B., Litvinov, I.A., and Sinyashin, O.G., Heteroatom Chem., 2011, vol. 22, no. 1, p. 1. https://doi.org/10.1002/hc20646

    Article  CAS  Google Scholar 

  18. Sadykova, Yu.M., Dalmatova, N.V., Voronina, Yu.K., Burilov, A.R., Pudovik, M.A., and Sinyashin, O.G., Heteroatom Chem., 2014, vol. 25, no. 1, p. 55. https://doi.org/10.1002/hc21135

    Article  CAS  Google Scholar 

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Funding

This work was financially supported by the Russian Foundation for Basic Research (project 20-03-00118, synthetic research) within the frame of the governmental task [physical and spectral studies (1H, 13C and 31P NMR, IR spectroscopy, MALDI-TOF spectrometry, elemental analysis)] using the equipment of the Collective Spectro-Analytical Center for Physicochemical Research of the Structure, Properties and Composition of Substances and Materials of the Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”.

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”, 420088, Kazan, Russia

    Yu. M. Sadykova, А. R. Burilov & М. А. Pudovik

  2. Kazan National Research Technological University, 420015, Kazan, Russia

    A. V. Zalaltdinova & А. K. Smailov

Authors
  1. Yu. M. Sadykova
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  2. A. V. Zalaltdinova
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  3. А. K. Smailov
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  4. А. R. Burilov
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  5. М. А. Pudovik
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Corresponding author

Correspondence to А. R. Burilov.

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No conflict of interest was declared by the authors.

Additional information

Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 7, pp. 1138–1142 https://doi.org/10.31857/S0044460X21070180.

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Sadykova, Y.M., Zalaltdinova, A.V., Smailov, А.K. et al. Synthesis of New Diaryl(hetaryl)ethylphosphonic Acids. Russ J Gen Chem 91, 1420–1423 (2021). https://doi.org/10.1134/S1070363221070215

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  • DOI: https://doi.org/10.1134/S1070363221070215

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