* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With malic acid In neat (no solvent) at 140℃; for 0.166667 h; Green chemistry
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.
91%
With ammonium acetate In neat (no solvent) at 114℃; for 0.0833333 h; Microwave irradiation
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.
91%
at 180℃;
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.
88%
With zinc(II) oxide In neat (no solvent) at 100℃; for 0.25 h; Microwave irradiation; Green chemistry
General procedure: A mixture of substituted 1,3-propanedione (0.5 g, 2.08 mmol, 1.0 eq.) and ZnO nanoparticles (1.0eq.) was heated in a microwave oven for 15 min. Same procedure used for purification of flavones as mentioned in the conventional heating method.
78%
at 100℃; for 1 h;
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. 6-Methoxyflavone (5a). Yield: 78percent; white solid, mp.: 163–165 °C; 1H-NMR (CDCl3) δ 7.93–7.80 (m,1H), 7.52 (t, J = 7.6 Hz, 2H), 7.51–7.39 (m, 1H), 7.24 (d, J = 3.1 Hz, 1H), 7.22 (d, J = 3.1 Hz, 2H), 7.19 (s,1H), 6.79 (s, 1H), 3.85 (s, 3H); 13C-NMR (CDCl3) δ 177.27, 162.12, 155.98, 150.04, 130.83, 130.46, 127.99,127.99, 125.20, 125.20, 123.52, 122.76, 118.48, 105.79, 103.81, 54.90. MS (ESI-MS) m/z calcd for C16H12O3[M + H]+: 253.26; found: 253.28.
Reference：
[1] Heterocycles, 1986, vol. 24, # 9, p. 2511 - 2517
[2] Letters in Organic Chemistry, 2014, vol. 11, # 8, p. 601 - 605
[3] Journal of Chemical Research, 2005, # 9, p. 556 - 557
[4] Letters in Organic Chemistry, 2015, vol. 12, # 8, p. 574 - 583
[5] Letters in Organic Chemistry, 2016, vol. 13, # 10, p. 734 - 741
[6] Asian Journal of Chemistry, 2019, vol. 31, # 5, p. 1133 - 1136
[7] Molecules, 2018, vol. 23, # 9,
[8] Journal of Chemical Research - Part S, 1998, # 6, p. 348 - 349
[9] Journal of the Chinese Chemical Society, 2004, vol. 51, # 6, p. 1389 - 1394
[10] Journal of the Chemical Society, 1950, p. 1252,1257
[11] Journal of Organic Chemistry, 1991, vol. 56, # 26, p. 7292 - 7297
[12] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 5, p. 770 - 773
[13] Synthetic Communications, 2013, vol. 43, # 11, p. 1549 - 1556
2
[ 104213-88-9 ]
[ 26964-24-9 ]
Yield
Reaction Conditions
Operation in experiment
92%
With dmap In N,N-dimethyl-formamide at 0 - 30℃; for 4 h; Inert atmosphere
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 NaHCO3, brine, dried over MgSO4, and filtered. The filtrate was concentrated in vacuo, and then the resulting residue was purified by column chromatography on silica gel to afford flavone 1 or 7. Spectral data of flavones 1a-1n and 7a-7c have been reported previously10.
Reference：
[1] Tetrahedron, 2011, vol. 67, # 51, p. 9993 - 9997
[2] Organic Letters, 2011, vol. 13, # 17, p. 4526 - 4529
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 1, p. 153 - 160
3
[ 87428-52-2 ]
[ 100-52-7 ]
[ 26964-24-9 ]
Yield
Reaction Conditions
Operation in experiment
89%
at 70℃; for 6 h;
In 10 ml in the reaction kettle, successively added 0.3183g (3mmol) benzaldehyde, 0.3323g (2mmol) 5-methoxy-2-hydroxy acetophenone and 0.2630g (0.6mmol) of the ionic liquid catalyst [Bmim]2[MoO4] (structural formula refer to embodiment 1), and 0.8170g (8mmol) tetrahydrofururyl alcohol solvent, stirring after mixing, heating to reaction temperature 70 °C, in 0.4 MPa stir to react under oxygen atmosphere 6h, cooled to the room temperature after the reaction, the solvent is removed by reduced pressure distillation after of tetrahydrofurfuryl alcohol, adding ethyl acetate and water extraction, the split-phase, passes through the column again chromatography and recrystallization of relative separation to obtain the target product 6-methoxy-flavone, the yield is 89percent, by nuclear magnetic resonance hydrogen spectrum, carbon spectrum and high-resolution mass spectrometry to determine its structural formula is:
Reference：
[1] Patent: CN105294627, 2016, A, . Location in patent: Paragraph 0097; 0098; 0099
4
[ 150-76-5 ]
[ 637-44-5 ]
[ 40547-03-3 ]
[ 26964-24-9 ]
Yield
Reaction Conditions
Operation in experiment
48%
With trifluoroacetic acid In chlorobenzene at 100℃; Inert atmosphere
General procedure: A mixture of Phenol derivatives (1) (1.0 mmol), trifluoromethanesulfonic acid (1.0 mmol) and propiolic acid (2a) (0.5 mmol) in PhCl (3.0 mL) was stirred at 100 °C for 1 h. After completion of reaction as indicated by TLC, the reaction mixture was poured into H2O, neutralized with NaHCO3 solution and extracted CH2Cl2. The organic layer was washed with 2M NaOH, dried over anhydrous MgSO4. The solvent was removed in vaccum, and the products were purified by silica gel columnchromatography (EtOAc-Hex) to give the desired product 3.
48%
With trifluorormethanesulfonic acid In chlorobenzene at 100℃; for 3 h;
The title compound was synthesized in the same manner as in Example 1, except that 4-methoxyphenol was used instead of phenol, 3-phenylpropiolic acid was used instead of propiolic acid, and the reaction time was 3 hours
With potassium hydroxide In water; acetone at 40℃; for 24 h;
6-Hydroxyflavone (8.39 mmol) was dissolved in acetone (2mL), potassium hydroxide (20.89 mmol), as base and water(117 μL) were added to reaction mixture, which turned intoa yellow solid; then, drop-wise dimethylsulfate (159 μL)was added and the mixture was heated at 40 °C for 24 h(monitored by TLC). The reaction mixture was washed withice water (2 mL) and filtered under vacuum. Finally, thesolid product (146.1 mg) was washed with NaOH (5percent), andthe mixture was shaken vigorously and filtered in vacuo toobtain 146.1 mg (yield of 63.8percent). Compound was recrystallizedfrom ethanol, with a melting point of 162–163 °C.
Reference：
[1] Organic Preparations and Procedures International, 2000, vol. 32, # 3, p. 280 - 283
17
[ 705-15-7 ]
[ 26964-24-9 ]
Reference：
[1] Journal of the Chinese Chemical Society, 2004, vol. 51, # 6, p. 1389 - 1394
[2] Journal of Organic Chemistry, 1991, vol. 56, # 26, p. 7292 - 7297
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 6, p. 1218 - 1231
[4] Molecules, 2018, vol. 23, # 9,
18
[ 127745-66-8 ]
[ 26964-24-9 ]
Reference：
[1] Journal of the Chinese Chemical Society, 2004, vol. 51, # 6, p. 1389 - 1394
[2] Journal of Organic Chemistry, 1991, vol. 56, # 26, p. 7292 - 7297
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 5, p. 770 - 773
[4] Molecules, 2018, vol. 23, # 9,
19
[ 672-13-9 ]
[ 26964-24-9 ]
Reference：
[1] Journal of Pharmaceutical Sciences, 1992, vol. 81, # 8, p. 812 - 814
[2] Organic Letters, 2011, vol. 13, # 17, p. 4526 - 4529
[3] Tetrahedron, 2011, vol. 67, # 51, p. 9993 - 9997
20
[ 104213-88-9 ]
[ 26964-24-9 ]
[ 38216-58-9 ]
Reference：
[1] Journal of Organic Chemistry, 1986, vol. 51, # 23, p. 4432 - 4436
[2] Journal of Organic Chemistry, 1986, vol. 51, # 23, p. 4432 - 4436
[3] Journal of Pharmaceutical Sciences, 1992, vol. 81, # 8, p. 812 - 814
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