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Study of Reactions between Fluoro-substituted Nucleogenic Phenyl Cations and Benzopyridine Derivatives

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Abstract

A study of ion-molecular reactions of fluoro-substituted phenyl cations with benzopyridine derivatives demonstrated the following: (a) at present only the nuclear-chemical method enables the reaction of a direct phenylation of the nitrogen atom in benzopyridine derivatives, which makes it possible to obtain previously unknown quaternized structures, and (b) generation of nucleogenic phenyl cations with various substituents leads to a simultaneous introduction of the required substituents into the aromatic ring at the nitrogen heteroatom. Quantum-chemical calculations additionally confirmed the assumption about the pathways of the ion-molecular reactions with nucleogenic phenyl cations.

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References

  1. Tolstaya, T.P., Ammonievye soedineniya, Khimicheskaya entsiklopediya v 5 tomakh (Ammonium Compounds, Chemical Encyclopedia in 5 vols.), Knunyants, I.L., Ed., Moscow: Sov. entsiklopediya, 1988, vol. 1.

  2. Tsarevsky, N.V., Slaveykova, V., Manev, S., et al., J. Chem. Educ, 1997, vol. 74, no. 6, p. 734.

    Article  CAS  Google Scholar 

  3. Onium Compounds-Advances in Research and Application, Acton, Q.A., Ed., Atlanta, Georgia: Scholarly Editions, 2013.

    Google Scholar 

  4. Lucac, M., Mojzis, J., Mojzisova, G., et al., Eur. J. Med. Chem., 2009, vol. 44, no. 12, p. 4970.

    Article  Google Scholar 

  5. Nefedov, VD., Toropova, M.A., Shchepina, N.E., et al., USSR Inventor’s Certificate no. 689 196, 1978.

  6. Hirsch, M., Dhara, S., and Diesendruck, C.E., Org. Lett., 2016, vol. 18, no. 5, p. 980.

    Article  CAS  Google Scholar 

  7. Arava, S. and Diesendruck, C.E., Synthesis, 2017, vol. 49, no. 16, p. 3535.

    Article  CAS  Google Scholar 

  8. Gopaul, K., Shintre, S.A, and Koorbanally, N.A., Med. Chem., 2015, vol. 15, no. 5, p. 631.

    CAS  Google Scholar 

  9. Park, B.K., Kitteringham, N.R., and O’Neill, P.M., Annu. Rev. Pharmacol. Toxicol., 2001, vol. 41, p. 443.

    Article  CAS  Google Scholar 

  10. Muller, K., Faeh, C., and Diederich, F., Science, 2007, vol. 317, p. 1881.

    Article  Google Scholar 

  11. Zhang, X.-J., Lai, T.-B., and Kong, R.Y.-C., Top. Curr. Chem., 2012, vol. 308, p. 365.

    Article  CAS  Google Scholar 

  12. Fluorinated Heterocyclic Compounds, Synthesis, Chemistry, and Applications, Petrov, V.A., Ed., Wiley, 2009.

  13. Uneyama, K., Organofluorine Chemistry, Oxford, UK: Blackwell, 2006.

    Book  Google Scholar 

  14. Fluorine in Medicinal Chemistry and Chemical Biology, Ojima, I., Ed., Chichester: Wiley-Blackwell, 2009.

    Google Scholar 

  15. Pausacker, K.H., Aust. J. Chem., 1958, vol. 11, no. 2, p. 200.

    Article  CAS  Google Scholar 

  16. Brody, F. and Ruby, P.R., Pyridine and Its Derivatives, Part I, The Chemistry of Heterocyclic Compounds, Klingsberg, E., Ed., New York: Interscience, 1960. vol. 14.

  17. Begue, J.-P. and Bonnet-Delpon, D., Bioorganic and Medicinal Chemistry of Fluorine, Hoboken, NJ, USA: Wiley, 2008.

    Book  Google Scholar 

  18. Shchepina, N.E., Avrorin, V.V., Badun, G.A., et al., Khim. Getertsikl. Soedin., 2012, vol. 542, no. 8, p. 1282.

    Google Scholar 

  19. Shchepina, N.E., Avrorin, V.V., Badun, G.A., et al., Vestn. Mosk. Gos. Univ., Ser. Khim., 2009, vol. 50, no. 5, p. 311.

    CAS  Google Scholar 

  20. Shchepina, N.E., Badun, G.A., Nefedov, V.D., et al., Tetrahedron Lett., 2002, vol. 43, p. 4123.

    Article  CAS  Google Scholar 

  21. Shchepina, N.E. and Avrorin, V.V., RF Patent no. 2 479 561, Publ. 20.04.2013, Byull. Izobret., 2013, no. 11, p. 927.

  22. Shchepina, N.E., Avrorin, V.V., Badun, G.A., et al., Radiokhimiya, 2016, vol. 58, no. 1, p. 84.

    Google Scholar 

  23. Pilyugin, G.T. and Krainer, Z.Ya., Dokl. Akad. Nauk SSSR, 1951, vol. 81, no. 4, p. 609.

    CAS  Google Scholar 

  24. Rogovik, M.I., Chernyak, I.N., Rozum, Yu.S., et al., Zh. Obshch. Khim., 1964, vol. 34, p. 3320.

    CAS  Google Scholar 

  25. Gilmore, B.F., Antimicrobial Ionic Liquids, Ionic Liquids: Applications and Perspectives, Kokorin, A., Ed., InTech, 2011, p. 586.

  26. Jauregui-Osoro, M., Sunassee, K., Weeks, A.J., et al., Eur. J. Nucl. Med. Mol. Imaging, 2010, vol. 37, no. 11, p. 2108.

    Article  CAS  Google Scholar 

  27. Granovsky, A.A., Firefly, Version 8.0.0. http://classic.chem.msu.su/gran/gamess/index.html.

  28. Schmidt, M.S., Baldridge, K.K., and Boatz, J.A., J. Comput. Chem., 1993, vol. 14, p. 1347.

    Article  CAS  Google Scholar 

  29. Shchepina, N.E., Avrorin, V.V., Badun, G.A., et al., Radiokhimiya, 2017, vol. 59, no. 3, p. 260.

    Google Scholar 

  30. Joule, J.A. and Mills, K., Heterocyclic Chemistry, Blackwell Science, 2010. 5th Ed.

  31. Brown, W.D. and Gouliaev, A.H., Synthesis, 2002, no. 1, p. 83.

  32. Davies, D.T., Aromatic Heterocyclic Chemistry (Oxford Chemistry Primers), Oxford: Oxford Univ. Press, 1992.

    Google Scholar 

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Authors and Affiliations

  1. Natural Science Institute, Perm State National Research University, Perm, 614990, Russia

    N. E. Shchepina

  2. St. Petersburg State University, St. Petersburg, 199034, Russia

    V. V. Avrorin

  3. Lomonosov Moscow State University, Moscow, 119991, Russia

    G. A. Badun

  4. Perm State National Research University, Perm, 614990, Russia

    S. N. Shurov

  5. Medical Center North, Vanderbilt University, Nashville, AA-1105, USA

    R. V. Shchepin

  6. Department of Chemistry, Biology, and Health Sciences (CBH), South Dakota School of Mines & Technology, Rapid City, 57701, USA

    R. V. Shchepin

Authors
  1. N. E. Shchepina
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  2. V. V. Avrorin
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  3. G. A. Badun
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  4. S. N. Shurov
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  5. R. V. Shchepin
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Correspondence to N. E. Shchepina.

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Russian Text © The Author(s), 2020, published in Radiochemistry, 2020, Vol. 62, No. 1, pp. 73–78.

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Shchepina, N.E., Avrorin, V.V., Badun, G.A. et al. Study of Reactions between Fluoro-substituted Nucleogenic Phenyl Cations and Benzopyridine Derivatives. Radiochemistry 62, 101–106 (2020). https://doi.org/10.1134/S1066362220010130

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  • DOI: https://doi.org/10.1134/S1066362220010130

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