Tandem one-pot synthesis of flavans by recyclable silica-HClO4 catalyzed Knoevenagel condensation and [4 + 2]-Diels-Alder cycloaddition.
Org Biomol Chem
; 10(26): 5143-50, 2012 Jul 14.
Article
em En
| MEDLINE
| ID: mdl-22648274
ABSTRACT
An efficient one-pot multi-component synthesis of flavans using perchloric acid supported on silica as a recyclable heterogeneous catalyst has been described. This is the first report of direct one-step construction of a flavan skeleton from a phenolic precursor. The method involves a Knoevenagel-type condensation leading to in situ formation of transient O-quinone methide which further undergoes [4 + 2]-Diels-Alder cycloaddition with styrene to yield a flavan skeleton. The method provides easy access to a wide range of bio-active natural products viz. flavonoids, anthocyanins and catechins.
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01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2012
Tipo de documento:
Article