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Pharmaceutical Chemistry Journal

, Volume 47, Issue 3, pp 172–175 | Cite as

A simple means of preparing quinoxaline derivatives: direct introduction of C-nucleophiles into the quinoxaline nucleus by substituting a hydrogen atom

  • Yu. A. Azev
  • E. D. Oparina
  • B. V. Golomolzin
  • O. S. Ermakova
  • V. S. Bakulev
Drug Synthesis Methods and Manufacturing Technology

Unsubstituted quinoxaline (I) reacts with dimedone, indanedione, and 1-phenyl-3-methylpyrazol-5-one in dimethylsulfoxide in the presence of acid to form monosubstitution products II – IV. Quinoxaline reacts with 1,3-dimethylbarbituric acid in dimethylsulfoxide solution at room temperature to form monosubstitution product V without external catalysis. Heating of I with resorcinol in ethanol in the presence of acid produced resorcinol derivative VI. In the presence of base, quinoxaline reacts with 1-phenyl-3-methylpyrazol-5-one to form dipyrazolylmethane VII and tetrapyrazolylethane derivative VIII. Compound VIII undergoes cleavage to form dipyrazolylmethane VII in dimethylformamide solution with boiling or in the presence of iodine at room temperature.

Keywords

quinoxaline reactions with nucleophiles 

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Yu. A. Azev
    • 1
  • E. D. Oparina
    • 1
  • B. V. Golomolzin
    • 1
  • O. S. Ermakova
    • 1
  • V. S. Bakulev
    • 1
  1. 1.Federal State Autonomic Higher Professional Educational Institution First President of Russia B. N. Eltsin Urals Federal UniversityEkaterinburgRussia

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