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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 12, pp 1179–1184 | Cite as

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

  • Antonina V. Popova
  • Galyna P. Mrug
  • Svitlana P. Bondarenko
  • Mikhaylo S. FrasinyukEmail author
Article
  • 17 Downloads

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.

Keywords

aurone enamine Mannich base o-quinone methide vinyl ether Diels–Alder reaction 

Notes

Supplementary material

10593_2019_2598_MOESM1_ESM.pdf (2.9 mb)
ESM 1 (PDF 2937 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Antonina V. Popova
    • 1
  • Galyna P. Mrug
    • 1
  • Svitlana P. Bondarenko
    • 2
  • Mikhaylo S. Frasinyuk
    • 1
    Email author
  1. 1.V. P. Kukhar Institute of Bioorganic Chemistry and PetrochemistryNational Academy of Sciences of UkraineKyivUkraine
  2. 2.National University of Food TechnologiesKyivUkraine

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