Benzothiophene-coumarin type compound and synthesis method thereof
A technology for coumarins and benzothiophenes, which is applied in the field of benzothienocoumarins and their synthesis, can solve the problems of low reaction yield, narrow substrate range, harsh reaction conditions and the like, and achieves a high yield High, direct response, easy separation effect
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Embodiment 1
[0044] Preparation of 8-methyl-6H-benzo[4,5]thieno[3,2-c]chromen-6-one
[0045]4-(4-methylphenylthio)coumarin (0.20mmol), palladium acetate (5mol%), silver acetate (0.40mmol) and propionic acid (1ml) were added as solvents to a 10ml dry Schlenk tube, Heat and stir at 140°C for 2 hours, monitor the progress of the reaction with TLC, extract with saturated sodium bicarbonate (3×5ml) and ethyl acetate (3×5ml) after the reaction is complete, combine the organic phases, dry and filter over anhydrous magnesium sulfate Concentrate and separate by silica gel column chromatography to obtain 44.63 mg of white powder with a yield of 85%. The structural formula of the resulting product is as follows:
[0046]
[0047] Such as figure 1 and figure 2 Shown, product NMR characterization: 1 HNMR (400MHz, CDCl 3 )δ8.52(s,1H),7.76(t,J=8.4Hz,2H),7.57-7.49(m,1H),7.45(d,J=8.2Hz,1H),7.33(t,J=9.1 Hz,2H),2.54(s,3H). 13 C NMR (101MHz, CDCl 3 )δ159.09, 157.64, 151.72, 140.04, 136.04, 132.58, ...
Embodiment 2
[0049] Preparation of 8-methyoxy-6H-benzo[4,5]thieno[3,2-c]chromen-6-one
[0050] Add 4-(4-methoxyphenylthio)coumarin (0.20mmol), palladium dichloride (10mol%), silver oxide (0.40mmol) and dimethylsulfoxide to a 10ml dry Schlenk tube (1.5ml) as solvent. Heat and stir at 140°C for 12 hours under sealing, monitor the progress of the reaction with TLC, extract with saturated sodium bicarbonate (3×5ml) and ethyl acetate (3×5ml) after the reaction is complete, combine the organic phases, dry and filter over anhydrous magnesium sulfate Concentrate and separate by silica gel column chromatography to obtain 45.12 mg of white powder with a yield of 80%. The structural formula of the resulting product is as follows:
[0051]
[0052] Such as image 3 and Figure 4 Shown, product NMR characterization: 1 H NMR (400MHz, CDCl 3 )δ8.19(d, J=2.3Hz, 1H), 7.76(d, J=8.7Hz, 2H), 7.55(t, J=7.7Hz, 1H), 7.47(d, J=8.2Hz, 1H) ,7.35(t,J=7.5Hz,1H),7.12(dd,J=8.8,2.4Hz,1H),3.96(s,3H). 13 CNMR (1...
Embodiment 3
[0054] Preparation of 8-fluoro-6H-benzo[4,5]thieno[3,2-c]chromen-6-one
[0055] Add 4-(2-fluorophenylthio)coumarin (0.20mmol), bistriphenylphosphine palladium dichloride (15mol%), copper acetate (0.20mmol) and ethanol ( 1ml) as solvent. Heat and stir at 60°C for 24 hours under sealing, monitor the progress of the reaction with TLC, extract with saturated sodium bicarbonate (3×5ml) and ethyl acetate (3×5ml) after the reaction is complete, combine the organic phases, dry and filter over anhydrous magnesium sulfate Concentrate and separate by silica gel column chromatography to obtain 43.78 mg of white powder with a yield of 81%. The structural formula of the resulting product is as follows:
[0056]
[0057] Such as Figure 5 and Figure 6 Shown, product NMR characterization: 1 H NMR (400MHz, CDCl 3 )δ8.51(d, J=8.0Hz, 1H), 7.83(dd, J=7.8, 1.4Hz, 1H), 7.62(t, J=7.1Hz, 1H), 7.56(dd, J=8.0, 5.1 Hz, 1H), 7.51(d, J=7.6Hz, 1H), 7.41(t, J=7.5Hz, 1H), 7.27–7.21(m, 1H). 13 C NM...
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