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Darzens reaction of 2-bromo-4,6-dimethoxy-3(2H)-benzofuranone with aromatic aldehydes to form flavonoids

✍ Scribed by Philipp A. Ottersbach; David Bolek; Eva Lepičová; Michael Gütschow; Martin Nieger

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
327 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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The applicability of 2‐bromo‐4,6‐dimethoxy‐3(2__H__)‐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 (R^1^ = H, R^2^ = R^3^ = OMe) was confirmed by X‐ray crystallographic analysis.

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