A copper-catalyzed, ligand-free intramolecular C−N coupling of (E)-2-(2-bromophenyl)-3-arylacrylamides has been developed. This protocol provides an efficient and practical synthetic route for the biologically important (E)-3-arylideneindolin-2ones from o-bromophenylacetic acids and aromatic or conjugated alkenyl aldehydes. Readily available starting materials, mild and noble metal-free conditions, high efficiency, and good tolerability for phenolic hydroxyl groups make this approach attractive and applicable.
A facile and practical approach for
the synthesis of natural coumestans
and derivatives starting from 2′,4′-dihydroxyl-3-arylcoumarins
has been developed. The process involved a seqential intramolecular
dehydrogenation/oxa-Micheal reaction efficiently promoted by 1,8-diazabicyclo[5.4.0]undec-7-ene
at 40 °C under metal- and ligand-free conditions with good functional
group compatibility.
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