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6-Hydroxyaurone aminomethyl derivatives in the inverse electron-demand Diels–Alder reaction

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Chemistry of Heterocyclic Compounds Aims and scope

The transformations of 7-dimethylaminomethyl-6-hydroxyaurone and 5-dimethylaminomethyl-6-hydroxy-7-methylurone in the inversed electron-demand hetero-Diels–Alder reaction were studied. As a result of in situ thermal formation of o-quinone methides containing the benzofuranone moiety and cycloaddition of cyclic vinyl esters, 2-benzylidene derivatives of difuro[2,3-b:2',3'-f]chromen-3(2H)-one, furo[2,3-f]pyrano[2,3-b]chromen-3(2H)-one, difuro[2,3-b:3',2'-g]chromen-3(2H)-one, and furo[3,2-g]pyrano[2,3-b]chromen-3(2H)-one heterocyclic systems were synthesized. A similar reaction with cyclic enamines, accompanied by subsequent transformation of hemi-aminals, led to the formation of partially hydrogenated derivatives of furo[2,3-a]xanthen-3(2H)-one and furo[3,2-b]xanthen-3(2H)-one.

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Authors and Affiliations

  1. V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1 Murmanska St., Kyiv, 02094, Ukraine

    Antonina V. Popova, Galyna P. Mrug & Mikhaylo S. Frasinyuk

  2. National University of Food Technologies, 68 Volodymyrska St., Kyiv, 01601, Ukraine

    Svitlana P. Bondarenko

Authors
  1. Antonina V. Popova
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  2. Galyna P. Mrug
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  3. Svitlana P. Bondarenko
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  4. Mikhaylo S. Frasinyuk
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Corresponding author

Correspondence to Mikhaylo S. Frasinyuk.

Additional information

Supplementary information file containing 1H and 13C NMR spectra of the synthesized compounds is available at the journal website http://link.springer.com/journal/10593.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(13), 1179–1184

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Popova, A.V., Mrug, G.P., Bondarenko, S.P. et al. 6-Hydroxyaurone aminomethyl derivatives in the inverse electron-demand Diels–Alder reaction. Chem Heterocycl Comp 55, 1179–1184 (2019). https://doi.org/10.1007/s10593-019-02598-z

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  • DOI: https://doi.org/10.1007/s10593-019-02598-z

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