1055316-75-0Relevant academic research and scientific papers
Darzens reaction of 2-bromo-4,6-dimethoxy-3(2H)-benzofuranone with aromatic aldehydes to form flavonoids
Ottersbach, Philipp A.,Bolek, David,Lepicova, Eva,Nieger, Martin,Guetschow, Michael
, p. 1149 - 1153 (2008)
(Chemical Equation Presented) 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.
