Skip to main content

Advertisement

SpringerLink
Log in

Investigation of Ion-Molecular Reactions of Nucleogenic Phenyl Cations with 1,4-Diazine Derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The use of nuclear-chemical synthesis, based on the generation of free nucleogenic phenyl cations, allowed for the direct phenylation of the nitrogen atom in 1,4-diazines. The presence of two methyl substituents in the quinoxaline substrate leads to a marked increase of diazine salt radiochemical yield. On the basis of quantum-chemical calculations the possibility of synthesizing 2,3-dimethyl-1,4-di-phenylquinoxalinium dication is proposed.

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

Fig. 1

Similar content being viewed by others

References

  1. W. Kaim, Angew. Chem., Int. Ed., 22, 171 (1983).

    Article  Google Scholar 

  2. G. W. H. Cheeseman, and E. S. G. Werstiuk, in: A. R. Katritzky (editor), Advances in Heterocyclic Chemistry, Vol. 14, Elsevier, New York (1972), p. 99.

    Google Scholar 

  3. V. I. Ivanskii, Chemistry of Heterocyclic Compounds, Vyssh. shkola, Moscow (1978), p. 348

    Google Scholar 

  4. A. F. Pozharskii, A.T. Soldatenkov, and A.R. Katritzky, Heterocycles in Life and Society, Wiley, New York (1997), p. 64.

    Google Scholar 

  5. A. Dell, D. H. Williams, H. R. Morris, G. A. Smith, J. Feeney, and G. C. K. Roberts, J. Am. Chem. Soc., 97, 2497 (1975).

    Article  CAS  Google Scholar 

  6. L. E. Seitz, W. J. Suling, and R. C. Reynolds, J. Med. Chem., 45, 5604 (2002).

    Article  CAS  Google Scholar 

  7. J. L. Sessler, H. Maeda, T. Mizuno, V. M. Lynch, and H. Furuta, Chem. Commun., 862 (2002).

  8. G. J. Kirkovits, R. S. Zimmerman, M. T. Huggins, V. M. Lynch, and J. L. Sessler, Eur. J. Org. Chem., 22, 3768 (2002).

    Article  Google Scholar 

  9. P. Ghosh and A. Mandal, Adv. Appl. Sci. Res., 2, № 1, 255 (2011).

    CAS  Google Scholar 

  10. A. Iwashita, K. Hattori, H. Yamamoto, J. Ishida, Y. Kido, K. Kamijo, K. Murano, H. Miyake, T. Kinoshita, M. Warizaya, M. Ohkubo, N. Matsuoka, and S. Mutoh, FEBS Lett., 579, 1389 (2005).

    Article  CAS  Google Scholar 

  11. M. M. Ghorab, F. A. Ragab, H. I. Heiba, M. G. El-Gazzar, and M. G. El-Gazzar, Acta Pharm., 61, 415 (2011).

    Article  CAS  Google Scholar 

  12. S. I. Kovalenko, I. S. Nosulenko, A. Yu. Voskoboynik, G. G. Berest, L. N. Antipenko, A. N. Antipenko, and A. M. Katsev, Med. Chem. Res., 22, 2610 (2013).

    Article  CAS  Google Scholar 

  13. K. Toshima, R. Takano, T. Ozawa, and S. Matsumura, Chem. Commun., 212 (2002).

  14. A. M. Sh. El-Sharief, and Z. Moussa, Eur. J. Med. Chem., 44, 4315 (2009).

    Article  CAS  Google Scholar 

  15. A. M. Almerico, M. Tutone, A. Guarcello, and A. Lauria, Bioorg. Med. Chem. Lett. 22, 1000 (2012).

    Article  CAS  Google Scholar 

  16. M. Asif, Med. Chem., 2, 151 (2012).

    Article  CAS  Google Scholar 

  17. G. V. Sidorov and N. F. Myasoedov, Russ. Chem. Rev., 68, 229 (1999). [Usp. Khim., 68, 254 (1999)].

    Article  CAS  Google Scholar 

  18. J. A. Egan, R. P. Nugent, and C. N. Filer, Appl. Radiat. Isot., 57, 837 (2002).

    Article  CAS  Google Scholar 

  19. J. A. Egan and C. N. Filer, J. Radioanal. Nucl. Chem., 258, 185 (2003).

    Article  CAS  Google Scholar 

  20. D. G. Ahern, A. G. Laseter, and C. N. Filer, Appl. Radiat. Isot., 65, 827 (2007).

    Article  CAS  Google Scholar 

  21. G. Mousseau, Q. Raffy, O. P. Thomas, M. Agez, R. Thai, J. P. Renaul, S. Pin, F. Ochsenbein, J.-C. Cintrat, and B. Rousseau, Biochemistry, 49, 4297 (2010).

    Article  CAS  Google Scholar 

  22. R. Simonsson, G. Stenhagen, C. Ericsson, and C. S. Elmore, J. Labelled Compd. Radiopharm., 56, 334 (2013).

    Article  CAS  Google Scholar 

  23. Y. Tian, Y. Hong, S. J. Bonacorsi, A. Balog, and S. Gong, J. Labelled Compd. Radiopharm., 57, 1 (2014).

    Article  CAS  Google Scholar 

  24. N. E. Shchepina, V. V. Avrorin, G. A. Badun, and G. A. Alexandrova, RU Patent 2320647, Bull. invent., № 9, 656 (2008).

  25. N. E. Shchepina, V. V. Avrorin, G. A. Badun, S. B. Lewis, and V. M. Fedoseev, Moscow Univ. Chem. Bull., 64, 244 (2009).

    Article  Google Scholar 

  26. 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, Chem. Heterocycl. Compd., 45, 796 (2009). [Khim. Geterotsikl. Soedinenii, 1008 (2009)].

    Article  CAS  Google Scholar 

  27. N. E. Shchepina, V. V. Avrorin, G. A. Alexandrova, and G. A. Badun, RU Patent 2442776, Bull. invent., No. 5, 341 (2012).

  28. N. E. Shchepina, V. V. Avrorin, G. A. Badun, N. A. Bumagin, S. B. Lewis, and S. N. Shurov, Org. Med. Chem. Lett., 2, 14 (2012).

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  30. N. E. Shchepina, V. V. Avrorin, G. A. Alexandrova, G. A. Badun, I. I. Boiko, and S. N. Shurov, Chem. Heterocycl. Compd., 49, 428 (2013). [Khim. Geterotsikl. Soedinenii, 461 (2013)].

    Article  CAS  Google Scholar 

  31. N. E. Shchepina, V. V. Avrorin, and G. A. Badun, Open J. Synth. Theor. Appl., 2, 51 (2013).

    Article  CAS  Google Scholar 

  32. A. K. Patidar, M. Jeyakandan, A. K. Moobiya, and G. Selvan, Int. J. PharmTech Res., 3, 386 (2011).

    CAS  Google Scholar 

  33. G. B. Barlin, The Chemistry of Heterocyclic Compounds. The Pyrazines, John Wiley & Sons (1982), p. 310.

  34. R. M. Anker and A. H. Cook, J. Chem. Soc., 489 (1944).

  35. D. Shelz and M. Priester, Helv. Chim. Acta, 58, 317 (1975).

    Article  Google Scholar 

  36. W. L. F. Armarego and C. Chai, Purification of Laboratory Chemicals, Butterworth-Heinemann (2012), p. 433

  37. T. J. Curphey and K. S. Prasad, J. Org. Chem., 37, 2259 (1972).

    Article  CAS  Google Scholar 

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

  39. L. G. Makarova and А. N. Nesmeyanov, Izv. AN SSSR, Ser. Khim., 617 (1945).

  40. G. T. Pilyugin and Z. Y. Krainer, Dokl. AN SSSR, 81, 609 (1951).

    CAS  Google Scholar 

  41. R. F. Staniychuk, G. T. Pilyugin, and O. E. Petrenko, Zh. Obshch. Khim., 40, 1834 (1970).

    Google Scholar 

  42. B. I. Ardashev and V. I. Minkin, Zh. Obshch. Khim., 29, 200 (1959).

    Google Scholar 

Download references

This work was supported by funding from the Ministry of Education and Science of the Russian Federation (baseline).

Author information

Authors and Affiliations

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

    N. E. Shchepina & I. M. Agafonova

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

    V. V. Avrorin

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

    G. A. Badun

  4. Perm State University, 15 Bukirev St., Perm, 614990, Russia

    A. N. Vasyanin & S. N. Shurov

Authors
  1. N. E. Shchepina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. V. Avrorin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. A. Badun
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. N. Vasyanin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. N. Shurov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. I. M. Agafonova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. E. Shchepina.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1735-1742, November, 2014.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shchepina, N.E., Avrorin, V.V., Badun, G.A. et al. Investigation of Ion-Molecular Reactions of Nucleogenic Phenyl Cations with 1,4-Diazine Derivatives. Chem Heterocycl Comp 50, 1595–1601 (2015). https://doi.org/10.1007/s10593-014-1629-6

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-014-1629-6

Keywords

Search

Navigation