Method for synthesizing pyrano-coumarin derivative

The technology of a coumarin derivative and a synthesis method is applied in the field of synthesis of coumarin derivatives, can solve the problems of expensive reagents, complicated process operation and the like, and achieves the effects of low cost, simple operation and mild reaction conditions

Inactive Publication Date: 2011-08-17
ZHEJIANG UNIV
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Problems solved by technology

However, the reported methods require expensive reagents or complicated process operations, so it is of great practical significance to find a method for preparing pyranocoumarin derivatives with low cost and simple operation.

Method used

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  • Method for synthesizing pyrano-coumarin derivative
  • Method for synthesizing pyrano-coumarin derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0017] 4-Hydroxycoumarin (10 mmol) and 1,3-diphenyl-2-propyn-1-ol (10 mmol) were dissolved in nitromethane and catalyzed by molecular iodine (1.0 mmol) React at 50°C for 1 hour, add 0.5 ml of sulfuric acid dropwise, stir overnight at 80°C, add 20 ml of saturated sodium sulfite solution, extract with 20×2 ml of ethyl acetate, dry the organic phase over anhydrous sodium sulfate, and concentrate under reduced pressure , and then purified by column chromatography to obtain 3,4-(2,4-diphenylpyrano)coumarin with a yield of 65%. The physical data of the product are: white solid; mp: 173-175°C; IR (KBr): 1716, 1631, 1610, 1493, 1454, 1387, 1271, 1205, 1169, 1112, 1013, 765, 698cm -1 ; 1 H-NMR (400MHz, CDCl 3 ): δ8.02(dd, J=1.6Hz, J=8.0Hz, 1H), 7.75-7.72(m, 2H), 7.59-7.55(m, 1H), 7.48-7.38(m, 6H), 7.36- 7.30(m, 3H), 7.25-7.21(m, 1H), 5.85(d, J=4.8Hz, 1H), 4.72(d, J=4.8Hz, 1H)ppm; 3 C-NMR (100MHz, CDCl 3 ): δ161.4, 155.6, 152.7, 146.8, 143.5, 132.5, 131.9, 129.2, 128.6, 128.6, 128....

Embodiment 2

[0019] 4-Hydroxycoumarin (10 mmol) and 3-phenyl-1-(3-methoxyphenyl)-2-propyn-1-ol (15 mmol) were dissolved in nitromethane, Molecular iodine (0.8 mmol) catalyzes the reaction at a temperature of 50°C for 1 hour, then drips 0.4 milliliters of sulfuric acid, stirs overnight at 100°C, adds 20 milliliters of saturated sodium sulfite, and extracts with 20×2 milliliters of ethyl acetate at the same time. Dry over sodium sulfate, concentrate under reduced pressure, and then purify by column chromatography to obtain 3,4-(2-phenyl-4-m-methoxyphenylpyrano)coumarin with a yield of 54%. The physical data of the product are:

[0020] white solid; mp: 144-146℃; IR(KBr): 1718, 1628, 1609, 1491, 1389, 1262, 1019, 766cm -1 ;

[0021] 1 H-NMR (400MHz, CDCl 3 ): δ8.00(d, J=8.0Hz, 1H), 7.73-7.71(m, 2H), 7.58-7.54(m, 1H), 7.46-7.32(m, 1H), 7.24-7.22(m, 1H ), 7.02-6.96(m, 2H), 6.77(dd, J=2.4Hz, J=8.4Hz, 1H), 5.83(d, J=4.2Hz, 1H), 4.68(d, J=4.2Hz, 1H ), 3.77(s, 1H)ppm; 3 C-NMR (100MHz, CDCl ...

Embodiment 3

[0023] 4-Hydroxycoumarin (10 mmol) and 3-phenyl-1-p-chlorophenyl-2-propyn-1-ol (12 mmol) were dissolved in nitroethane in molecular iodine ( 2.0 mmol) and react at 80°C for 1 hour, add 0.8 ml of sulfuric acid dropwise, stir overnight at 80°C, add 20 ml of saturated sodium sulfite, extract with 20×2 ml of ethyl acetate, and dry the organic phase over anhydrous sodium sulfate , concentrated under reduced pressure, and then purified by column chromatography to obtain 3,4-(2-phenyl-4-p-chlorophenylpyran)coumarin with a yield of 61%. The physical data of the product are: yellow solid; mp: 196-197°C; IR (KBr): 1724, 1629, 1611, 1493, 1388, 1113, 1015, 760cm -1 ;

[0024] 1 H-NMR (400MHz, CDCl 3 ): δ8.02-8.00(m, 1H), 7.74-7.72(m, 2H), 7.59-7.55(m, 1H), 7.48-7.32(m, 7H), 7.28-7.25(m, 2H), 5.79 (d, J=5.6Hz, 1H), 4.68 (d, J=5.6Hz, 1H) ppm; 13 C-NMR (100MHz, CDCl 3 ): δ161.4, 155.8, 152.7, 147.1, 142.0, 133.0, 132.4, 132.1, 129.8, 129.4, 128.7, 124.6, 124.2, 122.7, 116.8, 114.3, 10...

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Abstract

The invention discloses a method for synthesizing pyrano-coumarin derivative, comprising: 4-hydroxy coumarin and 1, 3-diaryl-2-allylene-1-alcohol are dissolved in organic solvent to react for 1h at the temperature of 50-80 DEG C under the catalysis of molecular iodine; concentrated sulfuric acid is then added into the reaction product, and the mixed solution is stirred at the temperature of 80-100 DEG C to react for 8-12h; then, saturated sodium sulfite solution is added, ethylacetate is used for extracting, and organic phase anhydrous sodium sulfate is dried and processed by reduced pressureconcentration; finally, after being purified by column chromatography, the pyrano-coumarin derivative can be obtained. The method has mild reaction condition, low cost, simple technique as well as convenient and fast operation.

Description

technical field [0001] The invention relates to a synthesis method of coumarin derivatives, especially a synthesis method of pyranocoumarin derivatives. Background technique [0002] Coumarin derivatives are an important structural component in natural products and drug synthesis, and have a wide range of physiological activities, such as anti-human immunodeficiency virus, antimalarial drugs, anticoagulants, etc., and are important in medicine. economic value. Some documents have reported the synthetic method of pyranocoumarin derivatives, for example, (1) document Tetrahedron, 2006,62,3016 has reported that isocyanate, butynedioic acid diethyl ester and 4-hydroxycoumarin Reaction prepares the method for pyranocoumarin derivative; (2) document Tetrahedron Letters2007,48,3299 has reported that benzaldehyde, malononitrile and 4-hydroxycoumarin use ammonium dihydrogen phosphate and (S)-proline Acid-reactive pyranocoumarin derivatives. However, the reported methods require ei...

Claims

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Application Information

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IPC IPC(8): C07D493/04
Inventor 戴西象毛侦军林旭锋
Owner ZHEJIANG UNIV
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