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DOI: 10.1055/s-0028-1088058
2-(Azidomethyl)arylboronic Acids in the Synthesis of Coumarin-Type Compounds
Publication History
Publication Date:
20 April 2009 (online)

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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References
Boronic acids 21a-c, like their precursors 4a,b coexist with anhydride forms of boronic acids with different degree of oligomerization. The NMR spectra of 21a-c derivatives purified by crystallization were rather complicated. On the other hand, when compounds 21a-c were isolated by column chromatography on silica gel, the NMR spectra of these products became almost fine due to the cleavage of the ether bonds in the associates.