Chemistry of Heterocyclic Compounds

, Volume 53, Issue 9, pp 1057–1060 | Cite as

Rearrangement of 4-oxoalkane-1,1,2,2-tetracarbonitriles in the directed synthesis of aryl-substituted 2-(3-cyano-5-hydroxy-1,5-dihydro-2H-pyrrol-2-ylidene)malononitriles

  • Mikhail Yu. BelikovEmail author
  • Sergey V. Fedoseev
  • Mikhail Yu. Ievlev
  • Oleg V. Ershov

3-Aryl-4-oxoalkane-1,1,2,2-tetracarbonitriles were synthesized by the interaction of 2-aryl ketones with tetracyanoethylene. Directed rearrangement of them in acetic acid in the presence of ammonium acetate led to the formation of 2-(3-cyano-5-hydroxy-1,5-dihydro-2Hpyrrol-2-ylidene)malononitriles containing an aryl substituent in conjugation with the acceptor buta-1,3-diene-1,1,3-tricarbonitrile moiety.


2-aryl ketones buta-1,3-diene-1,1,3-tricarbonitrile moiety 4-oxoalkane-1,1,2,2-tetracarbonitriles tetracyanoethylene rearrangement 


The study was carried out with the financial support of the Russian Foundation for Basic Research (project no 16-33-60156 mol_a_dk).


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© Springer Science+Business Media, LLC, part of Springer Nature 2017

Authors and Affiliations

  • Mikhail Yu. Belikov
    • 1
    Email author
  • Sergey V. Fedoseev
    • 1
  • Mikhail Yu. Ievlev
    • 1
  • Oleg V. Ershov
    • 1
  1. 1.Chuvash State University named after I. N. UlyanovCheboksaryRussia

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