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


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.


Ester Organic Chemistry Carbonyl Ketone Nitrile 
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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

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