Chemistry of Heterocyclic Compounds

, Volume 14, Issue 6, pp 601–605 | Cite as


VIII. Tetraalkyl-substituted 4-pyrylocyanines
  • A. I. Tolmachev
  • G. G. Dyadyusha
  • E. F. Karaban
  • A. A. Ishchenko
  • N. A. Derevyanko


Tetraalkyl-substituted 4-pyrolocyanines were synthesized and converted to pyridocyanines by reaction with methylamine. The exchange reaction proceeds particularly readily in the series of tetramethyl-substituted compounds, in which the oxygen atoms in one or both pyrylium residues can be replaced, depending on the conditions. It was established that, in contrast to the tetraphenyl-substituted compounds, among the tetramethyl-substituted compounds the symmetrical dyes (pyridinium derivatives) are more deeply colored than their oxygen-containing analogs. The reasons for this difference in the absorption spectra are analyzed thoroughly by the quantum-chemical method.


Oxygen Organic Chemistry Absorption Spectrum Pyridinium Oxygen Atom 
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.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    A. I. Tolmachev, N. A. Derevyanko, and M. A. Kudinova, Khim. Geterotsikl. Soedin., No. 5, 617 (1975).Google Scholar
  2. 2.
    A. I. Tolmachev, N. A. Derevyanko, E. F. Karaban, and M. A. Kudinova, Khim. Geterotsikl. Soedin., No. 5, 612 (1975).Google Scholar
  3. 3.
    A. I. Tolmachev, L. M. Shulezhko, and M. Yu. Kornilov, Ukr. Khim. Zh., 40, 286 (1974).Google Scholar
  4. 4.
    M. Yu. Kornilov, L. M. Shulezhko, and A. I. Tolmachev, Teor. Eksp. Khim., 10, 508 (1974).Google Scholar
  5. 5.
    M. Simalty, H. Strzelecka, and H. Khedija, Tetrahedron, 27, 3503 (1971).Google Scholar
  6. 6.
    R. Sprague and L. Brooker, J. Am. Chem. Soc., 59, 2697 (1937).Google Scholar
  7. 7.
    J. Wilt, G. Reynolds, and J. Van Allan, Tetrahedron, 29, 795 (1973).Google Scholar
  8. 8.
    B. I. Stepanov and L. P. Kazachenko, Opt. Spektrosk., 12, 131 (1962).Google Scholar
  9. 9.
    G. G. Dyadyusha and A. A. Ishchenko, in: Collection of Annotations of Programs for Molecular Spectroscopy [in Russian], Novosibirsk (1977), p. 22.Google Scholar
  10. 10.
    S. Hunig, B. Garner, G. Ruider, and W. Schenk, Ann., Nos. 5/6, 1036 (1973).Google Scholar
  11. 11.
    E. D. Sych, Zh. N. Belaya, and G. G. Dyadyusha, Ukr. Khim. Zh., 30, 1065 (1964).Google Scholar
  12. 12.
    Yu. A. Kruglyak, V. S. Kvakush, G. G. Dyadyusha, and V. I. Khil'chenko, Methods for Calculations in Quantum Chemistry. Calculation of the π-Electron Structures of Molecules by Simple Molecular Orbital Methods [in Russian], Naukova Dumka, Kiev (1967).Google Scholar
  13. 13.
    A. Balaban and C. Nenitzescu, Ann., 625, 74 (1959).Google Scholar

Copyright information

© Plenum Publishing Corporation 1978

Authors and Affiliations

  • A. I. Tolmachev
    • 1
  • G. G. Dyadyusha
    • 1
  • E. F. Karaban
    • 1
  • A. A. Ishchenko
    • 1
  • N. A. Derevyanko
    • 1
  1. 1.Institute of Organic ChemistryAcademy of Sciences of the Ukrainian SSRKiev

Personalised recommendations