Advertisement

Chemistry of Heterocyclic Compounds

, Volume 16, Issue 12, pp 1261–1267 | Cite as

Quaternary salts of quinolybenzimidazoles

  • I. V. Romanenko
  • A. K. Sheinkman
  • S. N. Baranov
  • V. N. Poltavets
  • N. A. Klyuev
Article
  • 54 Downloads

Abstract

The nitrogen atoms of the benzimidazole ring are alkylated initially in the quaternization of 2-(2-quinolyl)benzimidazole, and the nitrogen atom of the quinoline ring is alkylated only after this. Pyridyl- and quinolylbenzimidazoles and their quaternary salts were synthesized in order to study geometrical isomerism in the dihetaryl series. It was concluded that geometrical isomerism cannot occur in the case of the protonated forms or any other quaternary salts of dihetaryls, since as a result of the mutual electron-acceptor effect of the heteroaromatic cations the carbon-carbon bond between them is converted to a single σ bond, despite the fact that it is a bond between two sp2 carbon atoms.

Keywords

Nitrogen Organic Chemistry Carbon Atom Nitrogen Atom Quinoline 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    P. P. Zarin', É. S. Lavrinovich, and A. K. Aren, Khim. Geterotsikl. Soedin., No. 1, 104, 112 (1974).Google Scholar
  2. 2.
    C. Marzin, M. E. Peek, J. Elguero, H. P. Figeys, and N. Defay, Heterocycles, 6, 911 (1977).Google Scholar
  3. 3.
    N. A. Klyuev, A. K. Sheinkman, R. A. Khmel'nitskii, G. A. Mal'tseva, and N. R. Kal'-nitskii, Zh. Org. Khim., 13, 1079 (1977).Google Scholar
  4. 4.
    N. A. Klyuev, R. A. Khmel'nitskii, G. A. Mal'tseva, A. K. Sheinkman, V. A. Ivanov, and B. M. Zolotarev, Khim. Geterotsikl. Soedin., No. 7, 979 (1973).Google Scholar
  5. 5.
    P. L. Trakhtenberg, M. N. Zemtsova, A. N. Gusarov, A. N. Zvolinskii, and A. E. Lipkin, Khim. Geterotsikl. Soedin., No. 6, 751 (1979).Google Scholar
  6. 6.
    D. Jerchel, M. Kracht, and K. Krucker, Lieb. Ann., 590, 232 (1954).Google Scholar
  7. 7.
    B. A. Tertov and A. V. Koblik, Khim. Geterotsikl. Soedin., No. 5, 955 (1967).Google Scholar
  8. 8.
    V. I. Isagulyants and N. M. Anufrieva, Zh. Prikl. Khim., 46, 1389 (1973).Google Scholar
  9. 9.
    A. A. Polyakova and R. A. Khmel'nitskii, Mass Spectroscopy in Organic Chemistry [in Russian], Khimiya, Leningrad (1972).Google Scholar
  10. 10.
    R. A. Khmel'nitskii, N. A. Klyuev, and P. B. Terent'ev, Zh. Org. Khim., 7, 395 (1971).Google Scholar
  11. 11.
    H. Takuzo, and J. Masataka, Chem. Pharm. Bull., 22, 1923 (1974).Google Scholar
  12. 12.
    V. I. Minkin, O. A. Osipov, A. D. Garnovskii, and A. M. Simonov, Zh. Fiz. Khim., 36, 469 (1962).Google Scholar
  13. 13.
    B. V. Ioffe, Refractomeric Methods of Chemistry [in Russian], Khimiya, Leningrad (1974).Google Scholar
  14. 14.
    G. Hedestrand, Z. Phys. Chem., B, 428 (1929).Google Scholar
  15. 15.
    L. Yu. Akhadov, The Dielectric Properties of Pure Liquids [in Russian], Izd. Standartov, Moscow (1972).Google Scholar
  16. 16.
    O. A. Osipov, V. I. Minkin, and A. D. Garnovskii, Handbook of Dipole Moments [in Russian], Vysshaya Shkola, Moscow pp. 218, 236 (1971).Google Scholar
  17. 17.
    V. I. Minkin, O. A. Osipov, and Yu. A. Zhdanov, Dipole Moments in Organic Chemistry [in Russian], Khimiya, Leningrad (1968), p. 86.Google Scholar
  18. 18.
    O. A. Osipov, A. M. Simonov, V. I. Minkin, and A. D. Garnovskii, Zh. Fiz. Khim., 36, 1466 (1962).Google Scholar
  19. 19.
    A. K. Sheinkman, M. M. Mestechkin, A. P. Kucherenko, N. A. Klyuev, V. N. Poltavets, G. A. Mal'tseva, L. A. Palagushkina, and Yu. B. Vysotskii, No. 8, 1096 (1974).Google Scholar
  20. 20.
    A. K. Sheinkman, B. P. Zemskii, T. V. Stupnikova, Yu. B. Vysotskii, and A. N. Kost, Khim. Geterotsikl. Soedin., No. 11, 1477 (1978).Google Scholar
  21. 21.
    B. P. Zemskii, T. V. Stupnikova, A. K. Sheinkman, and Yu. B. Vysotskii, Zh. Org. Khim., 13, 2431 (1979).Google Scholar

Copyright information

© Plenum Publishing Corporation 1981

Authors and Affiliations

  • I. V. Romanenko
    • 1
  • A. K. Sheinkman
    • 1
  • S. N. Baranov
    • 1
  • V. N. Poltavets
    • 1
  • N. A. Klyuev
    • 1
  1. 1.Institute of Physical Organic Chemistry and Coal ChemistryAcademy of Sciences of the Ukrainian SSRDonetsk

Personalised recommendations