105285-13-0

Upstream product

• 105285-09-4 (E)-1-(2-hydroxy-6-methoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 699-83-2 2,6-dihydroxylacetophenone 
• 123-11-5 4-methoxy-benzaldehyde 
• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 

Downstream Products

• 51032-13-4 8-bromo-5-methoxy-2-(4-methoxy-phenyl)-chroman-4-one 
• 50879-50-0 3-Brom-4',5-dimethoxyflavanon 
• 29219-06-5 3-hydroxy-5-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 6697-63-8 5,4'-Dimethoxyflavone 

Relevant academic research and scientific papers

Synthesis of Flavonols via Pyrrolidine Catalysis: Origins of the Selectivity for Flavonol versus Aurone

A novel synthetic method for flavonol from 2′-hydroxyl acetophenone and benzaldehyde promoted by pyrrolidine under an aerobic condition in water is established. This protocol was supported by efficient synthesis of 44 common examples and three natural products. The α, β-unsaturated iminium ion (enimine ion E) was proved to be the key intermediate in the reaction. H218O and 18O2 isotope tracking experiments demonstrated that both water and the aerobic atmosphere were necessary to ensure the transformation. The selectivity for flavonol or aurone was originated from solvent-triggered intermediates, which were determined by UV-visible spectra from isolated enimine. The phenol-iminium E-A is dominant in water and the ketoenamine intermediate E-B is prevalent in acetonitrile. In the presence of pyrrolidine and oxygen, E-A leads to flavonol through E-I, a zwitterionic-like phenoloxyl-iminium ion, following the key steps of cyclization and a [2 + 2] oxidation; E-B proceeds through path II, a radical process induced by photolysis of E-B with both pyrrolidine and oxygen, to afford aurone. Preliminary mechanistic studies are reported.

Synthesis of 5-subsituted flavonols via the Algar-Flynn-Oyamada (AFO) reaction: The mechanistic implication

Herein, we report a synthetic method with improved selectivity for 5-substituted flavonols via the Algar-Flynn-Oyamada reaction (AFO), by using of sodium carbonate/hydrogen peroxide A series of 5-substituted flavonols was obtained with moderate to high yields. The mechanism of the AFO reaction was elucidated. LCMS analysis and in situ 1H NMR analysis indicated that the epoxide was involved in the transformation from chalcone to flavonol and/or aurone under alkaline base/peroxide conditions.

CONVERSION OF 2'-HYDROXYCHALCONES TO FLAVANONES CATALYZED BY COBALT SHIFF BASE COMPLEX

Co(salpr) catalyzes the conversion of 2'-hydroxychalcones to flavanones in methanol under oxygen.Base catalysis by Co(salpr) (OH) produced in situ is responsible for the reaction, which is found to proceed reversibly.

HETEROCYCLES. XIX. REACTION OF 2'-HYDROXYCHALCONES WITH ALKALINE HYDROGEN PEROXIDE

Reaction of 2'-hydroxychalcones, which contain the hydroxyl and/or the methoxyl group at the 4- and 6'-positions, with alkaline hydrogen peroxide has been examined.It is observed that these substituents intricately influence the formation of the products.