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Phenylhydeazones of α-keto acids, containing the isoxazoline ring, and their anomalous behavior in the feofilaktov reaction

  • Organic and Biological Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The reaction of the esters of phenylazoacetonedicarboxylic acid with hydroxylamine gave three products in ratios that depended on the structure of the radical of the ester group: the esters of the phenyl-hydrazone of 2-isoxazolin-5-on-3-ylglyoxylic acid (IIa), the esters of 4-phenylazo-3-isoxazolin-5-on-3-ylacetic acid (III), and 2-phenyl-4-carbalkoxymethyl-5-carbalkoxytriazoles (IV).

  2. 2.

    The phenylhydrazones (II) and phenylazo compounds (III), which contain an isoxazoline ring, are resistant to chemical reduction in neutral medium; aniline is not cleaved and the isoxazoline ring is not opened during catalytic hydrogenation.

  3. 3.

    The phenylazoacetonedicarboxylic acid esters have an azoenol structure.

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Authors and Affiliations

  1. Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, USSR

    V. M. Belikov, T. F. Savel'eva & E. N. Safonova

Authors
  1. V. M. Belikov
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  2. T. F. Savel'eva
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  3. E. N. Safonova
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2060–2067, September, 1973.

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Belikov, V.M., Savel'eva, T.F. & Safonova, E.N. Phenylhydeazones of α-keto acids, containing the isoxazoline ring, and their anomalous behavior in the feofilaktov reaction. Russ Chem Bull 22, 2006–2011 (1973). https://doi.org/10.1007/BF00929393

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  • DOI: https://doi.org/10.1007/BF00929393

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