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

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.

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Figure 1.

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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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Correspondence to Mikhail Yu. Belikov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(9), 1057–1060

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Belikov, M.Y., Fedoseev, S.V., Ievlev, M.Y. et al. 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. Chem Heterocycl Comp 53, 1057–1060 (2017). https://doi.org/10.1007/s10593-017-2170-1

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Keywords

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