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Multicomponent synthesis of new barbituric acid derivatives

  • M. N. Elinson,
  • A. N. Vereshchagin,
  • Yu. E. Ryzhkova,
  • K. A. Karpenko,
  • T. M. Iliyasov,
  • V. M. Kalashnikova,
  • M. P. Egorov

摘要

A new type of the four-component tandem Knoevenagel—Michael reaction was discovered, which used arylaldehydes, N,N′-dimethylbarbituric acid, dimedone, and morpholine or piperidine in organic solvents or in water. The reaction proceeded under mild conditions at room temperature with the formation of a new substituted unsymmetrical polycyclic ionic scaffold in 83–98% yields. The structures of the reaction products were confirmed by X-ray diffraction analysis on the example of two compounds. The further oxidative cyclization of the Knoevenagel—Michael reaction products led to unsymmetrical substituted dihydrofurans spiro-annulated with N,N′-dimethylbarbituric acid. The structures of the synthesized compounds were confirmed by X-ray diffraction analysis.