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Coumarin-based homoisoflavonoids as precursors in the synthesis of 8-heteroarylmethylcoumarins

CHEMISTRY OF HETEROCYCLIC COMPOUNDS(2023)

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Abstract
series of homoisoflavonoids bearing 3-(het)arylcoumarin moiety were synthesized by cascade reaction of enaminones with 8-dimethyl- aminomethyl-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-(1 H -pyrazol-4-ylmethyl)coumarins, 7-hydroxy-8-(isoxazol-4-ylmethyl)- coumarins, and 7-hydroxy-8-(pyrimidin-5-ylmethyl)coumarins.
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Key words
coumarins,homoisoflavonoids,pyrazoles,pyrimidines,inverse electron-demand Diels–Alder reaction
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