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Chemistry of Heterocyclic Compounds

, Volume 51, Issue 9, pp 829–833 | Cite as

Condensation of 1,2-diamino-4-phenylimidazole and N-arylmaleimides with the formation of new tetrahydroimidazo[1,5-b]pyridazines

  • Dmitriy Yu. VandyshevEmail author
  • Khidmet S. Shikhaliev
  • Andrei Yu. Potapov
  • Mikhail Yu. Krysin
Article

We studied the condensation of 1,2-diamino-4-phenylimidazole with N-arylmaleimides and established that this reaction occurred upon brief refluxing of reactants in isopropanol in the presence of a catalytic amount of acetic acid and produced substituted 7-amino-N-aryl-2-oxo-5-phenyl-1,2,3,4-tetrahydroimidazo[1,5-b]pyridazine-4-carboxamides. Performing this reaction at room temperature led to the acyclic intermediates N-aryl-3-(1,2-diamino-4-phenylimidazol-5-yl)pyrrolidine-2,5-diones.

Keywords

7-amino-2-oxo-1,2,3,4-tetrahydroimidazo[1,5-b]pyridazine-4-carboxamides N-arylmaleimides 1,2-diamino-4-phenylimidazole bisnucleophiles regioisomers 

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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Dmitriy Yu. Vandyshev
    • 1
    Email author
  • Khidmet S. Shikhaliev
    • 1
  • Andrei Yu. Potapov
    • 1
  • Mikhail Yu. Krysin
    • 1
  1. 1.Voronezh State UniversityVoronezhRussia

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