Abstract
Several 2-(azidomethyl)arylboronic acids were synthesized. Their
involvement into organolead-mediated Pinhey arylation reaction with
4-hydroxycoumarins afforded 3-[2-(azidomethyl)aryl]-4-hydroxycoumarins
or [4,3-c ]isoquinolinocoumarins
in reasonable yields via two- or four-step one-pot reaction sequence.
Palladium-catalyzed cross-coupling of organoboron reagents with
4-trifluoromethylsulfonyloxycoumarins under Suzuki reaction conditions
gave 4-[2-(azidomethyl)aryl]coumarins in good yields.
2-(Azidomethyl)arylboronic acid, as well as azide-containing iso-
and neoflavonoid compounds underwent catalytic alkyne-azide cycloaddition
in THF-water, providing 1,4-triazole compounds regioselectively
in good to excellent yields.
Key words
coumarins - azides - arylation - cross-coupling - cycloaddition
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