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Synthesis of 2-dimethylamino-3-substituted 2h-pyrans and study of their valence isomerization to δ-dimethylamino dienones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It is shown that 2-dimethylamino-3-isopropyl(3-dimethylamino)-2H-pyrans are formed in the condensation of aminal acetals of α-isopropyl-or α-dimethylamino-Β-dimethylaminoacroleins with Β-dicarbonyl compounds. It was observed by means of 1H and 13C NMR and UV spectroscopy that they do not undergo valence isomerization to δ-dimethylamino dienones. Under the influence of pulse photoexcitation the 2H-pyrans undergo reversible cleavage of the C-O bond and isomerization to the corresponding dienones.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, 117913, Moscow

    Zh. A. Krasnaya, T. S. Stytsenko, V. S. Bogdanov & A. S. Dvornikov

Authors
  1. Zh. A. Krasnaya
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  2. T. S. Stytsenko
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  3. V. S. Bogdanov
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  4. A. S. Dvornikov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1325–1333, October, 1983.

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Krasnaya, Z.A., Stytsenko, T.S., Bogdanov, V.S. et al. Synthesis of 2-dimethylamino-3-substituted 2h-pyrans and study of their valence isomerization to δ-dimethylamino dienones. Chem Heterocycl Compd 24, 1095–1103 (1988). https://doi.org/10.1007/BF00475681

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  • DOI: https://doi.org/10.1007/BF00475681

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