Advertisement

Chemistry of Heterocyclic Compounds

, Volume 28, Issue 3, pp 304–308 | Cite as

Synthesis of the alkaloid dioxyline and other 6,7-dimethoxyisoquinolines in a modified ritter reaction

  • V. G. Brovchenko
  • N. V. Shibaeva
  • A. I. Pyshchev
  • E. V. Kuznetsov
Article
  • 37 Downloads

Abstract

It has been found that aceto- and benzonitriles and 3,4-dimethoxyphenylacetone in the presence of acetylperchlorate or upon heating in polyphosphoric acid or polyphosphoric ester form the corresponding isoquinoline. The data indicate that the reaction proceeds like a typical Ritter reaction and is defined by electrophilic activation of the carbonyl group of the ketone and the nucleophilicity of the nitrile. This methodology gave the alkaloid dioxyline (dimoxyline), obtained in high yield by the use of benzoylhexachloroantimonate.

Keywords

Ester Organic Chemistry Carbonyl Ketone Nitrile 
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.
    W. Zelinski, Pol. J. Chem., 56, 93 (1982).Google Scholar
  2. 2.
    E. N. Zil'berman, Reactions of Nitrites [in Russian], Khimiya, Moscow (1972), p. 285.Google Scholar
  3. 3.
    D. Barton and D. Ollis (eds.), General Organic Chemistry, Vol. 3 [Russian translation], Khimiya, Moscow (1982), p. 647.Google Scholar
  4. 4.
    M. Shamma and J. L. Moniot, Isoquinoline Alkaloids Research, 1972–1977, Plenum Press, New York (1978).Google Scholar
  5. 5.
    D. Barton and D. Ollis (eds.), General Organic Chemistry, Vol. 8 [Russian translation], Khimiya, Moscow (1985), p. 255.Google Scholar
  6. 6.
    G. N. Dorofeenko, E. I. Sadekova, and E. V. Kuznetsov, Preparative Pyrilium Salt Chemistry [in Russian], Rostov University Publishing House, Rostov-on-Don (1972).Google Scholar
  7. 7.
    L. Fieser and M. Fieser, Reagents for Organic Synthesis, Vol. 3 [Russian translation], Mir, Moscow (1970), p. 146.Google Scholar
  8. 8.
    M. N. Galbraith and W. B. Whalley, J. Chem. Soc. (C), 3557 (1971).Google Scholar
  9. 9.
    M. J. Amer, B. Z. Booth, Gh. F. M. Noori, and P. M. F. Proenca, Jr., J. Chem. Soc., Perkin I, No. 5, 1075 (1983).Google Scholar
  10. 10.
    I. B. Korobka, A. V. Bicherov, I. B. Shcherbakova, G. N. Dorofeenko, and E. V. Kuznetsov, Zh. Org. Khim., 18, No. 5, 589 (1982).Google Scholar
  11. 11.
    S. M. Luk'yanov and S. V. Borodaev, Zh. Obshch. Khim., 22, No. 3, 510 (1986).Google Scholar
  12. 12.
    G. N. Dorofeenko, S. V. Krivyn, and E. I. Sadekova, Khim. Geterotsikl. Soedin., No. 6, 730 (1971).Google Scholar
  13. 13.
    E. Shepard, J. Noth, H. Porter, and C. Simmans, J. Am. Chem. Soc., 74, 4611 (1952).Google Scholar
  14. 14.
    G. N. Dorofeenko, S. B. Krivyn, Yu. A. Zhdanov, and E. I. Sadekova, Dokl. Akad. Nauk SSSR, 181, 345 (1968).Google Scholar
  15. 15.
    G. N. Dorofeenko, A. D. Semenov, V. I. Dulenko, and S. V. Krivyn, Zh. Org. Khim., 2, 1492 (1966).Google Scholar

Copyright information

© Plenum Publishing Corporation 1992

Authors and Affiliations

  • V. G. Brovchenko
    • 1
  • N. V. Shibaeva
    • 1
  • A. I. Pyshchev
    • 1
  • E. V. Kuznetsov
    • 1
  1. 1.Physical and Organic Chemical Research InstituteRostov State UniversityRostov-on-Don

Personalised recommendations