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Diene synthesis with 2-pyrones and 2-pyridones. 31. Stereochemistry of the successive addition of two different dienophiles to 2-pyrones

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Abstract

The stereochemistry of the successive addition of two different dienophiles, viz., N-phenylmaleinimide and 4-phenyl-1,2,4-triazoline-3,5-dione, to 2-pyrones was studied. The configurations of the mixed adducts (bisimides) obtained were established by PMR and mass spectrometry. It is shown that in all cases the reactions proceed with the formation of mixtures of syn and anti isomers, the ratios of which depend on the positions of the methyl groups in the starting 2-pyrones.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, Moscow

    T. L. Nesterova, N. P. Shusherina, V. A. Shmorgunov & P. B. Terent'ev

Authors
  1. T. L. Nesterova
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  2. N. P. Shusherina
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  3. V. A. Shmorgunov
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  4. P. B. Terent'ev
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Additional information

See [1] for communication 30.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1471–1476, November, 1982.

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Nesterova, T.L., Shusherina, N.P., Shmorgunov, V.A. et al. Diene synthesis with 2-pyrones and 2-pyridones. 31. Stereochemistry of the successive addition of two different dienophiles to 2-pyrones. Chem Heterocycl Compd 18, 1139–1143 (1982). https://doi.org/10.1007/BF00506359

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  • DOI: https://doi.org/10.1007/BF00506359

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