Darzens reaction of 2-bromo-4,6-dimethoxy-3(2H)-benzofuranone with aromatic aldehydes to form flavonoids
Philipp A. Ottersbach
Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany
Search for more papers by this authorDavid Bolek
Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany
Search for more papers by this authorEva Lepičová
Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany
Search for more papers by this authorMichael Gütschow
Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany
Search for more papers by this authorMartin Nieger
Laboratory of Inorganic Chemistry, Department of Chemistry, University of Helsinki, PO Box 55, FIN-00014 University of Helsinki, Finland
Search for more papers by this authorPhilipp A. Ottersbach
Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany
Search for more papers by this authorDavid Bolek
Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany
Search for more papers by this authorEva Lepičová
Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany
Search for more papers by this authorMichael Gütschow
Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany
Search for more papers by this authorMartin Nieger
Laboratory of Inorganic Chemistry, Department of Chemistry, University of Helsinki, PO Box 55, FIN-00014 University of Helsinki, Finland
Search for more papers by this authorAbstract
The applicability of 2-bromo-4,6-dimethoxy-3(2H)-benzofuranone (1) to produce flavonoid-derived epoxides in the course of the Darzens reaction with aldehydes was investigated. However, instead of the epoxides, flavonols 3 and, in certain cases, benzofuranyl-substituted flavonols 4 were isolated. The generation of 3 is assumed due to a ring expansion of the initially formed epoxides. These flavonols can react with 1 to produce the unexpected 1:2 adducts 4 as minor products. The structure of the hexamethoxy derivative 4b (R1 = H, R2 = R3 = OMe) was confirmed by X-ray crystallographic analysis.
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