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Synthetic method for chromone compound
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A technology of chromone compounds and compounds, applied in the field of synthesis of chromone compounds, can solve the problems of low substituent tolerance, limited reaction substrate raw materials, low reaction yield, etc.
Inactive Publication Date: 2011-08-03
TSINGHUA UNIV
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Problems solved by technology
The traditional synthesis methods of chromone derivatives generally have the disadvantages of harsh reaction conditions, limited raw materials for reaction substrates, low tolerance of substituents, and low reaction yields.
Recently, the technology of palladium-catalyzed synthesis of chromone derivatives has also been developed, but the price of palladium metal is relatively high, and it has high toxicity
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Embodiment 1
[0053]
[0054] Add 70 mg of K to a Schlenk test tube equipped with a magnetic stir bar 2 CO 3 , 158.5mg 1-(2-bromophenyl)-3-p-tolyl-1,3-dione, 2mL DMF, reaction temperature 100°C, reaction time 1h, product passed petroleumether / ethyl acetate=10 : 1 (v / v) for separation and purification, the product obtained was 115 mg of 2-p-tolyl chromone, and the yield was 97%.
[0058] Add 70 mg of K to a Schlenk test tube equipped with a magnetic stir bar 2 CO 3 , 151mg 1-(2-bromophenyl)-3-phenyl-1,3-dione, 2mLDMF, reaction temperature 100°C, reaction time 1h, product through petroleumether / ethyl acetate=10:1( v / v) Separation and purification were carried out to obtain 101 mg of 2-phenylchromone with a yield of 91%.
[0059] 2-Phenylchromone: The boiling point is 100-101°C. 1 H NMR (300MHz, CDCl 3 , ppm) δ8.24(dd, J=7.91Hz, 1H), 7.94(m, 2H), 7.71(t, J=7.7Hz, 1H), 7.55(m, 4H), 7.43(t, J=7.5 Hz, 1H), 6.84(s, 1H). 13 C NMR (75MHz, CDCl 3 , ppm) δ178.7, 163.7, 156.6, 134.1, 132.1, 131.9, 129.3, 126.6, 126.0, 125.5, 124.2, 118.4, 107.9. ESI-MS [M+H] + m / z 223.4.
Embodiment 3
[0061]
[0062] Add 70 mg of K to a Schlenk test tube equipped with a magnetic stir bar 2 CO 3, 169mg 1-(2-bromophenyl)-3-(4-chlorophenyl)-1,3-dione, 2mL DMF, reaction temperature 100°C, reaction time 1h, the product was passed through petroleumether / ethyl acetate Ester=10:1 (v / v) for separation and purification to obtain 123 mg of 2-(4-chlorophenyl)chromone with a yield of 96%.
[0063] 2-(4-substituted phenyl) chromone: the boiling point is 187-191°C. 1 H NMR (300MHz, CDCl 3 , ppm) δ8.23(d, J=7.9Hz, 1H), 7.86(d, J=8.6Hz, 2H), 7.71(t, J=7.7Hz, 1H), 7.55(m, 3H), 7.43( t, J=7.5Hz, 1H), 6.80(s, 1H). 13 C NMR (75MHz, CDCl 3 , ppm) δ178.4, 162.4, 156.3, 138.0, 134.1, 130.4, 129.5, 127.7, 125.8, 125.5, 124.0, 118.2, 107.8. ESI-MS [M+H] + m / z 257.5.
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Abstract
The invention discloses a synthetic method for a chromone compound, which comprises the following steps: in the normal pressure and under the reaction condition of 100 DEG C, taking ortho-position halogenated aromatic ring substituting group diketone as raw material, DMF or DMSO as a dissolvent, and alkali carbonate (including sodium, potassium, caesium and the like) as alkalis so as to efficiently synthesize chromone compound in the condition of an organic catalyst. Compared with the conventional synthetic method for chromone compound, the synthetic method does not need metalcatalysis and takes DMF or DMSO as the reactive solvent, medium and strong alkalis such as alkali carbonate are taken as alkali, reaction conditions are mild; the amount of catalysismetal does not need to be controlled; the yield of the chromone compound is high, and the chromone compound has high tolerance on multiple functional groups of the aromatic ring.
Description
technical field [0001] The invention relates to a method for generating chromone compounds through Ullmann reaction under metal-free catalysis to realize aryl C-O bonding. Background technique [0002] Aryl C-O bond formation is a very important type of reaction in the field of organic chemistry, which is widely involved in the preparation of a series of natural products, biological reagents, drugs, fragrances, cosmetics and polymers. The traditional method of realizing C-O bonding is to use copper to catalyze the Ullmann reaction between bromobenzene or iodobenzene and phenol to prepare aromatic ethers. This method generally requires very harsh reaction conditions. In a strong alkaline environment, a strong polar solvent Among them, it is obtained by long-term reaction under the catalysis of copper in measurement units. Later, palladium-catalyzed and improved copper-complex catalyzed C–O bond formation under relatively mild conditions were realized. However, metals are in...
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