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

Nataliia V. Myshko, Galyna P. Mrug, Kostyantyn M. Kondratyuk, Svitlana P. Bondarenko, Mykhaylo S. Frasinyuk
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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.


Keywords


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

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