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Investigation of the phenylation of methyl-quinolines using tritium-labeled nucleogenic phenyl cations

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Chemistry of Heterocyclic Compounds Aims and scope

The phenylation of methylquinolines by nucleogenic phenyl cations was studied. This reaction led to a product mixture through electrophilic addition and electrophilic substitution, with composition depending on the methyl substituent position. In the case of 4-methylquinoline, the electron-donating methyl group in the para position markedly increased the yield of N-phenylquinolinium derivative, while the low yield of the quinolinium salt in the case of 8-methylquinoline was due to the two factors - low basicity of the nitrogen atom in comparison to 4-methylquinoline and steric hindrance by the methyl group, which led to predominant electrophilic substitution.

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References

  1. K. H. Pausacker, Austr. J. Chem., 11, 200 (1958).

    Article  CAS  Google Scholar 

  2. G. T. Pilyugin and B. M. Gutsulyak, Usp. Khim., 32, 389 (1963).

    Article  Google Scholar 

  3. T. L. Gilchrist, Heterocyclic Chemistry [Russian translation], Mir, Moscow (1996).

    Google Scholar 

  4. A. R. Katritzky and A. F. Pozharskii, Handbook of Heterocyclic Chemistry, Pergamon, Amsterdam (2000).

    Google Scholar 

  5. G. T. Pilyugin and Z. Ya. Krainer, Dokl. Akad. Nauk SSSR, 8, 609 (1951).

    Google Scholar 

  6. G. T. Pilyugin and B. M. Gutsulyak, Zh. Obshch. Khim., 29, 3076 (1959).

    CAS  Google Scholar 

  7. G. T. Pilyugin, S. V. Shinkorenko, O. M. Stankevich, and V. V. Stankevich, Khim. Geterotsikl. Soedin., 406 (1966). [Chem. Heterocycl. Compd., 2, 295 (1966)].

    Google Scholar 

  8. G. T. Pilyugin, Yu. S. Rozum, Yu. O. Gorichok, and B. M. Gutsulyak, Zh. Obshch. Khim., 35, 506 (1965).

    CAS  Google Scholar 

  9. I. I. Boiko, S. V. Shinkorenko, E. P. Opanasenko, and V. V. Lizin, Zh. Org. Khim., 21, 859 (1985).

    CAS  Google Scholar 

  10. C. D. Geddes, P. Douglas, C. P. Moore, T. J. Wear, and P. L. Egerton, J. Heterocycl. Chem., 36, 949 (1999).

    Article  CAS  Google Scholar 

  11. O. I. Tolmachev, N. V. Pilipchuk, O. D. Kachkovsky, Yu. L. Slominski, V. Ya. Gaivoronsky, E. V. Shepelyavyy, S. V. Yakunin, and M. S. Brodyn, Dyes Pigm., 74, 195 (2007).

    Article  CAS  Google Scholar 

  12. B. M. Gutsulyak, Usp. Khim., 41, 346 (1972).

    Article  CAS  Google Scholar 

  13. S. V. Shinkorenko, T. G. Pilyugin, I. I. Sidorchuk, and V. M. Yavorskii, Khim.-Farm. Zh., 6, No. 1, 25 (1972).

    Google Scholar 

  14. I. I. Sidorchuk, R. F. Stadniichuk, E. N. Tishchenko, and L. T. Bordyakovskaya, Khim.-Farm. Zh., 12, No.7, 78 (1978).

    CAS  Google Scholar 

  15. V. I. Voznayk, L. G. Savitskaya, and D. D. Neporadnyi, Khim.-Farm. Zh., 18, 951 (1984).

    Google Scholar 

  16. R. M. Abd El-Aal and M. Younis, Bioorg. Chem., 32, 193 (2004).

    Article  CAS  Google Scholar 

  17. J. A. Joule and K. Mills, Heterocyclic Chemistry [Russian translation], Mir, Moscow (2009).

    Google Scholar 

  18. Yu. V. Zatsikha, B. M. Gutsulyak, and Yu. O. Gorichok, Fiziolog. Aktivnye Veshchestva, 6, 218 (1971).

    Google Scholar 

  19. N. E. Shchepina, V. V. Avrorin, G. A. Badun, and G. A. Alexandrova, RF. Pat. 2320647; Byul. Izobr. RF, No. 9, 656 (2008).

  20. N. E. Shchepina, V. V. Avrorin, G. A. Badun, G. A. Alexandrova, S. E. Ukhanov, V. M. Fedoseev, S. B. Lewis, and I. I. Boiko, Khim. Geterotsikl. Soedin., 1008 (2009) [Chem. Heterocycl. Compd., 45, 796 (2009)].

    Google Scholar 

  21. D. T. Davies, Aromatic Heterocyclic Chemistry, Oxford University Press, Oxford (1992), p. 46.

    Google Scholar 

  22. M. Sainsbury, Heterocyclic Chemistry, Royal Society of Chemistry, Cambridge (2001), p. 43.

    Google Scholar 

  23. D. W. Brown and A. H. Gouliaev, Synthesis, 83 (2002).

  24. A. R. Katritzky, Handbook of Heterocyclic Chemistry, Pergamon, Oxford (1985), p. 153.

    Google Scholar 

  25. H. C. Brown, D. H. McDaniel, and O. Häfliger, in: E. A. Braude and F. C. Nachod (editors), Determination of Organic Structures by Physical Methods, Vol. 1, Academic Press, New York (1955), p. 567.

  26. R. Yang and S. G. Schulman, Luminescence, 16, 129 (2001).

    Article  CAS  Google Scholar 

  27. R. S. Hosmane and J. F. Liebman, Struct. Chem., 20, 693 (2009).

    Article  CAS  Google Scholar 

  28. S. G. Schulman and A. C. Capomacchia, J. Am. Chem. Soc., 95, 2763 (1973).

    Article  CAS  Google Scholar 

  29. I. N. Chernyak, V. E. Pridan, V. A. Bazhutin, and M. Yu. Kornilov, Zh. Obshch. Khim., 44, 1584 (1974).

    Google Scholar 

  30. N. E. Shchepina, V. V. Avrorin, G. A. Alexandrova, and G. A. Badun, RF Pat. 2442776; Byul. Izobr. RF, No. 5, 341 (2012).

  31. http://classic.chem.msu.su/gran/firefly/index.html.

  32. N. E. Shchepina, V. V. Avrorin, G. A. Alexandrova, I. N. Kir’yanova, G. A. Badun, and I. I. Boiko, Perspektivnye Materialy, Spets. Vyp., No. 8, 211 (2010).

  33. N. E. Shchepina, V. V. Avrorin, G. A. Badun, S. B. Lewis, and S. E. Ukhanov, Khim. Geterotsikl. Soedin., 320 (2012) [Chem. Heterocycl. Compd., 48, 301 (2012)].

    Google Scholar 

  34. Y. Cheng, J. Wang, and O. Meth-Cohn, ARKIVOC, xiii, 89 (2005).

  35. K. Lava, Y. Evrard, K. Van Hecke, L. Van Meervelt, and K. Binnemans, RSC Adv., 2, 8061 (2012).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Natural Sciences Institute, Perm State University, 4 Genkel St., Perm, 614990, Russia

    N. E. Shchepina & G. A. Alexandrova

  2. Saint Petersburg State University, 7/9 Universitetskaya Nab., 199034, Saint Petersburg, Russia

    V. V. Avrorin

  3. M. V. Lomonosov Moscow State University, 1, Build. 3, Leninskie Gory, Moscow, 119991, Russia

    G. A. Badun

  4. “Technolog Co. Ltd”, 2/157 Mendeleeva St., Pereslavl-Zalessky, 152025, Russia

    I. I. Boiko

  5. Perm State National Research University, 15 Bukirev St., Perm, 614990, Russia

    S. N. Shurov

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  1. N. E. Shchepina
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  2. V. V. Avrorin
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  3. G. A. Alexandrova
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  4. G. A. Badun
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  5. I. I. Boiko
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  6. S. N. Shurov
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Correspondence to N. E. Shchepina.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 461-467, March, 2013.

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Shchepina, N.E., Avrorin, V.V., Alexandrova, G.A. et al. Investigation of the phenylation of methyl-quinolines using tritium-labeled nucleogenic phenyl cations. Chem Heterocycl Comp 49, 428–434 (2013). https://doi.org/10.1007/s10593-013-1264-7

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  • DOI: https://doi.org/10.1007/s10593-013-1264-7

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