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Features of 3-amino-5-methylisoxazole in heterocyclizations involving pyruvic acids

The chemical properties of 3-amino-5-methylisoxazole in the reactions involving pyruvic acid derivatives are reported. The multicomponent condensation of 3-amino-5-methylisoxazole, aromatic aldehyde, and pyruvic acid was not effective while the treatment of the starting amine with pyruvic acid derivatives led to suitable synthetic procedures for selective synthesis of furanones and pyrrolones. It was established that only NH2-nucleophilic center of 3-amino-5-methylisoxazole takes part in the heterocyclizations with pyruvic acid derivatives.

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Correspondence to Valentyn A. Chebanov.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(1), 78–89

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Morozova, A.D., Muravyova, E.A., Shishkina, S.V. et al. Features of 3-amino-5-methylisoxazole in heterocyclizations involving pyruvic acids. Chem Heterocycl Comp 55, 78–89 (2019). https://doi.org/10.1007/s10593-019-02422-8

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Keywords

  • 3-amino-5-methylisoxazole
  • furanones
  • pyrrolones
  • pyruvic acids
  • heterocyclization