7-METHOXYFLAVONE

General procedure: The mixture of 1-(2-hydroxyphenyl)-3-aryl-1, 3-propanedione 1a (0.5 g) and malic acid (1.0 eq.) was heatedeither in an oil bath, preheated at 140 °C for 10 min or in amicrowave reactor for 5 min. After the completion of reaction(TLC check), the reaction mixture was allowed to cool;at room temperature water (10 mL) and ethyl acetate (10mL) were added. Reaction mixture was neutralized by additionof solid NaHCO3. Organic layer was separated and theaqueous layer was extracted in ethyl acetate (2 10 mL).Combined organic extract was dried over anhydrous sodiumsulfate and concentrated in vacuo. The crude product waspurified by column chromatography on silica gel using hexane-ethylacetate solvent system to give the correspondingflavones in high yield.General procedure: The mixture of 1-(2-hydroxyphenyl)-3-aryl-1, 3-propanedione 1a (0.5 g, 2.08 mmol) and ammonium acetate (0.16 g, 2.08 mmol) was heated either in an oil bath, preheated at 114°C for 10 min or in a microwave reactor for 5min. After the pH of the reaction mixture was brought back to 7.0 by the careful addition of NaHCO3 solution. The aqueous layer was extracted with ethyl acetate, dried(Na2SO4), and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using hexane-ethyl acetate solvent system to give the corresponding flavones in high yield.General procedure: The mixture of 1-(2-hydroxyphenyl)-3-aryl-1, 3-propanedione 4a-q (0.5g, 2.08 mmol) and L-ascorbic acid(3.7g, 2.08 mmol) was heated on a preheated oil bath or undermicrowave irradiation at 180 °C for 2-3 min. After completionof reaction (TLC check), the reaction mixture wascooled to room temperature and the flask was sonicated byadding excess water. The crude product was filtered oversuction-pump and washed with excess of water to removeL-ascorbic acid. The solid obtained was dried and crystallizedby using ethanol to give the corresponding flavones inhigh yield. The purity of products was confirmed by satisfactoryspectroscopic data.General procedure: Compounds 4a–j (1.8 g) glycerol triacetate (10 mL) and concentrated sulfuric acid (0.4 mL) wereplaced in a round bottomed flask equipped with a reflux condenser, stirred about 1 h at 100 C andthen the mixture was poured into a beaker containing 50 g of crushed ice, where solids were formedafter stirring and then filtered from the solution, Next the solids were washed with water until the acidwas removed. Finally, the solids were purified and separated by column chromatography eluting witha mixed petroleum ether and ethyl acetate solvent until the final products 5a–j were obtained.General procedure: 2'-Hydroxyacetophenone (1 mmol) and substituted aromatic aldehyde (1 mmol) were mixed together along with pyrrolidine (0.5 mmol) and iodine (0.05 mmol) in DMSO solvent (10 mL). The resulting mixture was then heated at 150 °C for the given time. After completion of reaction (monitored by TLC) the reaction mass was allowed to cool and diluted with ethyl acetate (20 mL). Resulting solution was then washed with water and saturated sodium thiosulfate solution followed by drying over anhydrous sodium sulfate and concentrating under reduced pressure to furnish the crude product. The residue obtained was purified by column chromatography using petroleum ether-ethyl acetate as an eluent to afford flavones (3a–r).General procedure: To a solution of o-alkynoylphenol 3 or 6 in DMF (4 mL/mmol) was added DMAP (10 mol percent) at 0 °C under argon. After being stirred at 30 °C, the reaction mixture was diluted with water. The aqueous layer was extracted twice with ethyl acetate. The organic layer was washed with 1 M HCl, saturated aqueous NaHCOIn 10 ml in the reaction kettle, successively added 0.3183g (3mmol) benzaldehyde, 0.3323g (2mmol) 4-methoxy-2-hydroxy acetophenone and 0.2630g (0.6mmol) of the ionic liquid catalyst [Bmim]EXAMPLE 3 Synthesis of 7-Hydroxy-2-phenyl-chromen-4-one (Compound 3) 100 mg (0.4 mmol) of compound The invention also pertains to each of the following compounds: ... 2-[4-(dimethylamino)phenyl]-4H-chromen-4-one; 1-(benzyloxy)-2-phenyl-1H-imidazo[4, 5-b]pyridine; 2-(benzylthio)-4-phenyl-5-(1-phenyl-1H-1, 2, 3, 4-tetraazol-5-yl)pyrimidine; 6-fluoro-2-phenyl-4H-chromen-4-one;

Molecular Weight:252.26
XLogP3:3.9
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:252.078644241
Monoisotopic Mass:252.078644241
Topological Polar Surface Area:35.5
Heavy Atom Count:19
Complexity:368
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes