Chemistry of Heterocyclic Compounds

, Volume 20, Issue 2, pp 170–176 | Cite as

1,4-Dihydropyridine-3,5-di-and 2-methyl-4-aryl-5-oxo-4,5-dihydro-1H-indeno[1,2-b]pyridine-3-carbothionic acid ethyl esters

  • B. A. Vigante
  • Ya. Ya. Ozols
  • G. Ya. Dubur
  • E. M. Belash
  • Yu. I. Beilis
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Abstract

Methods for the synthesis of 1,4-dihydropyridine-3,5-di- and 4-aryl-5-oxo-4,5-dlhydro-1H-indeno[1,2-b]pyridine-3-carbothionic acid ethyl esters were developed. A comparative analysis of the physicochemical characteristics of this series of substances is given.Their reactivities in electrochemical and chemical oxidation reactions were studied. The electrochemical oxidation potentials of the thionic acid esters are found in a lower anodic range as compared with their oxygen analogs. According to the ionization constants, the thionic acid esters of 4,5-dihydroindenopyridines are stronger acids than the carbonyl esters; this is explained by participation of the free 3d orbitals of the sulfur atom in stabilization of the anion.

Keywords

Oxidation Ester Carbonyl Oxidation Reaction Ethyl Ester 
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.
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Literature cited

  1. 1.
    F. Bossert and W. Vater, Naturwissenschaften, 58, 578 (1971).Google Scholar
  2. 2.
    M. Iwanami, T. Shibanuma, M. Fujimoto, R. Kawai, K. Tamazawa, T. Takenada, K. Takahashi, and M. Murakami, Chem. Pharm. Bull., 27, 1426 (1979).Google Scholar
  3. 3.
    B. Loev, M. M. Goodman, M. K. Snader, R. Tedeschi, and E. Macko, J. Med. Chem., 17, 956 (1974).Google Scholar
  4. 4.
    G. Ya. Dubur, Yu.A. Zilber, A. Kh. Velena, A. O. Kumerova, and G. D. Tirzit, Izv. Akad. Nauk Latv. SSR, No.7, 65 (1975).Google Scholar
  5. 5.
    B. A. Vigante, Ya. Ya. Ozols, G. Ya. Dubur, E. M. Beilis, and V. V. Prezhdo, Khim. Geterotsikl. Soedin., No. 2, 219 (1982).Google Scholar
  6. 6.
    B. A. Biganti, Ya. Ya. Ozols, and G. Ya. Dubur, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 6, 707 (1980).Google Scholar
  7. 7.
    S. Scheithauer and H. Pech, East German Patent No. 94361; Chem. Abstr., 79, 5176 (1973).Google Scholar
  8. 8.
    A. J. Bridges and G. H. Whitham, J. Chem. Soc., Perkin Trans. I, No. 16, 1603 (1975).Google Scholar
  9. 9.
    P. J. Brignell, U. Eisner, and P. S. Farrell, J. Chem. Soc. (B), No. 11, 1083 (1966).Google Scholar
  10. 10.
    F. Duus, in: Comprehensive Organic Chemistry, Vol. 3, Sulphur, Selenium, Silicon, Boron, and Organometallic Compounds, D. Neville Jones, ed., Pergamon Press (1979), p. 377.Google Scholar
  11. 11.
    T. Durst, ibid., in: Comprehensive Organic Chemistry, Vol. 3, Sulphur, Selenium, Silicon, Boron, and Organometallic Compounds, D. Neville Jones, ed., Pergamon Press (1979), p.172.Google Scholar
  12. 12.
    H. Bredereck, G. Simchen, and B. Funke, Chem. Ber., 104, 2709 (1971).Google Scholar
  13. 13.
    A. Kamal, R. Akhtar, T. Begum, and A. A. Qureshi, Pak. J. Sci. Ind. Res., 14, 6 (1971); Chem. Abstr., 75, 124751 (1971).Google Scholar
  14. 14.
    Ya. P. Stradyn', Yu. I. Beilis, Ya. R. Uldrikis, G. Ya. Dubur, A. E. Sausin', and B. S. Chekavichus, Khim. Geterotsikl. Soedin., No. 11, 1525 (1975).Google Scholar
  15. 15.
    Ya. R. Uldrikis, A. O. Kumerova, and G. Ya. Dubur, Khim. Geterotsikl. Soedin., No. 5, 691 (1973).Google Scholar
  16. 16.
    A. Albert and E. Serjeant, Ionization Constants of Acids and Bases, Wiley (1962).Google Scholar
  17. 17.
    S. Oae, The Chemistry of Organic Sulfur Compounds [Russian translation], Khimiya, Moscow (1975), p. 24.Google Scholar
  18. 18.
    N. V. Kondratenko, V. I. Popov, A. A. Kolomeitsev, E. P. Saenko, V. V. Prezhdo, A. E. Lutskii, and L. M. Yagupol'skii, Zh. Org. Khim., 16, 1215 (1980).Google Scholar
  19. 19.
    L. M. Yagupol'skii, A. Ya. Il'ichenko, and V. N. Kondratenko, Usp. Khim., 43, 64 (1974).Google Scholar
  20. 20.
    D. Cram, Fundamentals of Carbanion Chemistry, Academic Press (1965).Google Scholar
  21. 21.
    Ya. P. Stradyn', G. Ya. Dubur, Yu. I. Beilis, Ya. R. Uldrikis, and A. F. Korotkova, Khim. Geterotsikl. Soedin., No. 1, 84 (1972).Google Scholar

Copyright information

© Plenum Publishing Corporation 1984

Authors and Affiliations

  • B. A. Vigante
    • 1
    • 2
  • Ya. Ya. Ozols
    • 1
    • 2
  • G. Ya. Dubur
    • 1
    • 2
  • E. M. Belash
    • 1
    • 2
  • Yu. I. Beilis
    • 1
    • 2
  1. 1.Institute of Organic SynthesisAcademy of Sciences of the Latvian SSRRiga
  2. 2.Kharkov Institute of Public NutritionKharkov

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