Advertisement

Chemistry of Heterocyclic Compounds

, Volume 15, Issue 1, pp 23–28 | Cite as

Synthesis and properties of 4-ethoxyfluoranthenopyrylium salts and fluoranthenopyrones

  • M. I. Shenbor
  • A. S. Azarov
Article

Abstract

The mutual effect of the parts of the fluoranthene molecule was studied in the case of the pyrylation reactions of isomeric o-hydroxy ketones of fluoranthene [11-hydroxy-12-acetyl-(phenylene part) (I) and 4-hydroxy-3-acetyl-fluoranthene (naphthalene part) (I′)]. Pyrylium salts were obtained, and the yields were higher from I than from I′; this indicates conjugation of the π-electron systems of the parts of the fluoranthene molecule. Fluorantheneopyrones and their derivatives were also obtained. It is shown that the mutual effect of the parts of the fluoranthene molecules does not have a substantial influence on the results of the reactions that take place in the pyrone ring. The structures of the compounds obtained were proved by alternative synthesis.

Keywords

Organic Chemistry Phenylene Ketone Naphthalene Mutual Effect 
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.
    M. I. Shenbor, V. I. Tikhonov, and A. S. Azarov, Zh. Org. Khim., 12, 1069 (1976).Google Scholar
  2. 2.
    M. I. Shenbor, A. S. Azarov, and S. N. Denisenko, Zh. Org. Khim., 13, 2411 (1977).Google Scholar
  3. 3.
    G. N. Dorofeenko and V. V. Tkachenko, Khim. Geterotsikl. Soedin., No. 8, 1033 (1972).Google Scholar
  4. 4.
    G. N. Dorofeenko and V. V. Tkachenko, Zh. Org. Khim., 8, 2188 (1972).Google Scholar
  5. 5.
    G. N. Dorofeenko, V. V. Mezheritskii, and N. A. Lopatina, Khim. Geterotsikl. Soedin., No. 8, 1112 (1971).Google Scholar
  6. 6.
    G. N. Dorofeenko, V. V. Tkachenko, and V. V. Mezheritskii, Khim. Geterotsikl. Soedin., No. 4, 465 (1975).Google Scholar
  7. 7.
    E. Clar and J. E. Stephen, Tetrahedron, 20, 1559 (1964).Google Scholar
  8. 8.
    G. Dzhoshi Usha and G. S. Amin, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 2, 267 (1960).Google Scholar
  9. 9.
    M. Bloch and S. Kostanecki, Ber., 33, 471 (1900).Google Scholar
  10. 10.
    V. V. Virkar and T. S. Wheeler, J. Chem. Soc., No. 11, 1680 (1939).Google Scholar
  11. 11.
    S. Kostanecki and J. Tambor, Ber., 33, 333 (1900).Google Scholar
  12. 12.
    B. A. Kazanski (editor), Organic Syntheses [Russian translation], Collective Vol. 4, Inostr. Lit., Moscow (1953), p. 517.Google Scholar
  13. 13.
    J. M. Heilbron, D. H. Hey, and B. Lythgol, J. Chem. Soc., No. 3, 295 (1936).Google Scholar
  14. 14.
    I. I. Grandberg and A. N. Kost, Zh. Obshch. Khim., 32, 3025 (1962).Google Scholar
  15. 15.
    M. I. Shenbor and A. S. Azarov, Zh. Org. Khim., 14, 1942 (1978).Google Scholar

Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • M. I. Shenbor
    • 1
  • A. S. Azarov
    • 1
  1. 1.F. É. Dzerzhinskii Dnepropetrovsk Institute of Chemical TechnologyDnepropetrovsk

Personalised recommendations