3-aryl coumarin derivatives and preparation method thereof
A technology for aryl coumarin and derivatives, which is applied in the field of 3-aryl coumarin derivatives and its preparation, can solve the problems of by-product formation, long reaction time, high cost, etc., and achieve mild reaction conditions and raw materials Inexpensive, easy to obtain, and easy to operate
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Embodiment 1
[0041] Example 1. R=-H, R 1 =R 2 When =-H, the preparation of 3-phenylcoumarin derivatives
[0042] Add KMnO to the 50mL reaction bottle 4 (1.0mmol, 158mg) and 10mL of glacial acetic acid were refluxed at 120°C for 20min; after the solution returned to room temperature, coumarin (0.5mmol, 73mg) and phenylboronic acid (1.0mmol, 122mg) were added to the solution, at 80 ℃ in an oil bath for 0.5 h; after the reaction, remove the insoluble matter by filtration, and add saturated NaHCO to the filtrate 3 The solution was neutralized to neutral, extracted twice with 15mL ethyl acetate, and the extract was washed twice with saturated brine; the extract was washed with anhydrous Na 2 SO 4 After drying and concentration under reduced pressure, it was separated and purified by column chromatography (eluent: ethyl acetate / petroleum ether=1 / 10) to obtain 0.094 g of a colorless powdery solid with a yield of 85.0%.
[0043]
[0044] Melting point: 140-141°C. 1 H NMR (400MHz, CDCl 3 ...
Embodiment 2
[0045] Example 2. R=-OCH 3 , R 1 =R 2 Preparation of 3-(3,4,5-trimethoxy)phenylcoumarin derivatives when =-H
[0046] Add KMnO to the 50mL reaction bottle 4 (1.0mmol, 158mg) and 10mL acetic anhydride, refluxed at 120°C for 20min; after the solution returned to room temperature, coumarin (0.5mmol, 73mg) and 3,4,5-trimethylphenylboronic acid were added to the solution (1.0mmol, 212mg), stirred and reacted in an 80°C oil bath for 2h; after the reaction, pour the reaction solution into 20g of ice-water mixture, stir to precipitate solid, then stand for suction filtration, wash the filter cake with water until the filtrate is near the middle properties, the filter cake was dried and then recrystallized with ethyl acetate and petroleum ether to obtain 0.129 g of a colorless powdery solid with a yield of 83.0%.
[0047]
[0048] Melting point: 137-138°C. 1 H NMR (400MHz, CDCl 3 )δ:7.81(s,1H),7.56-7.50(m,2H),7.33(d,J H-H =8.2Hz,1H),7.29(td,J H-H =7.4Hz,J H-H =1.0Hz,1H),6.9...
Embodiment 3
[0049] Embodiment 3.R=-F, R 1 =R 2 When =-H, the preparation of 3-(3-fluorophenyl)coumarin derivatives
[0050] Add KMnO to the 50mL reaction bottle 4 (1.0mmol, 158mg) and 10mL propionic acid were refluxed at 120°C for 20min; after the solution returned to room temperature, coumarin (0.5mmol, 73mg) and m-fluorophenylboronic acid (1.0mmol, 140mg) were added to the solution, Stir the reaction in an oil bath at 60°C for 0.5h; after the reaction, remove the insoluble matter by filtration, and add saturated NaHCO to the filtrate 3 The solution was neutralized to neutral, extracted twice with 15mL ethyl acetate, and the extract was washed twice with saturated brine; the extract was washed with anhydrous Na2SO4 4 After drying and concentration under reduced pressure, it was separated and purified by column chromatography (eluent: ethyl acetate / petroleum ether=1 / 6) to obtain 0.108 g of a colorless powdery solid with a yield of 90.0%.
[0051]
[0052] Melting point: 173-174°C. ...
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