COUMARIN-BASED HOMOISOFLAVONOIDS AS PRECURSORS IN THE SYNTHESIS OF 8-HETEROARYLMETHYLCOUMARINS

Authors

  • Nataliia V. Myshko V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Science of Ukraine, 1 Akademika Kukharya St., Kyiv 02094, Ukraine
  • Galyna P. Mrug V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Science of Ukraine, 1 Akademika Kukharya St., Kyiv 02094, Ukraine
  • Kostyantyn M. Kondratyuk V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Science of Ukraine, 1 Akademika Kukharya St., Kyiv 02094, Ukraine
  • Svitlana P. Bondarenko National University of Food Technologies, 68 Volodymyrska St., Kyiv 01601, Ukraine
  • Mykhaylo S. Frasinyuk V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Science of Ukraine, 1 Akademika Kukharya St., Kyiv 02094, Ukraine Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine

DOI:

https://doi.org/10.1007/7882

Keywords:

coumarins, homoisoflavonoids, pyrazoles, pyrimidines, inverse electron-demand Diels–Alder reaction.

Abstract

A series of homoisoflavonoids bearing 3-(het)arylcoumarin moiety were synthesized by cascade reaction of enaminones with 8-dimethylaminomethyl-7-hydroxy-3-(het)arylcoumarins. The further reaction of synthesized coumarin-isoflavone hybrids with bidentate nucleophiles led to the formation of substituted 7-hydroxy-8-(1H-pyrazol-4-ylmethyl)coumarins, 7-hydroxy-8-(isoxazol-4-ylmethyl)coumarins, and 7-hydroxy-8-(pyrimidin-5-ylmethyl)coumarins.

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Published

2023-08-09

Issue

Vol. 59 No. 6/7 (2023): Ukrainian impact on heterocyclic chemistry after the three decades of independence

Section

Original Papers