A method for preparing 4-aminoiminocoumarin derivatives
A technology of coumarin derivatives and aminoimine, applied in the direction of organic chemistry and the like, can solve the problems of complex process and low yield, and achieve the effects of improving reaction efficiency, simple post-processing, and good industrial application prospects.
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Embodiment 1
[0021] Add 2 mg of CuI catalyst, 24 mg of o-hydroxybenzonitrile, 22 μL of phenylacetylene and 20 μL of p-toluenesulfonyl azide into a 10 ml reaction tube, then add 1 ml of dichloromethane, and drop 40 mg of triethylamine into the reaction tube after nitrogen replacement. The reaction mixture was heated at 80°C for 4 h, the mixture was filtered, washed three times with petroleum ether / ethyl acetate (volume ratio 5 / 1, 10 mL), the filtrate was combined and concentrated, and separated by column chromatography, the eluent was petroleum ether / ethyl acetate Ethyl acetate (volume ratio 1 / 1) 600ml, the final product N-(4-amino-3-phenyl-chromene-2-ylidene)-4-methyl-benzenesulfonamide was obtained with a yield of 95% . 1 H NMR(500MHz,DMSO)δ = 8.27 (d, J=10.0 Hz, 1H), 7.81 (d, J=10.0 Hz, 2H), 7.70 (t, J=10.0Hz, 1H), 7.51 (t, J =5.0 Hz , 2H), 7.44 – 7.40 (m, 3H), 7.32 – 7.28 (m, 4H),2.32 (s, 3H); 13 C NMR (126 MHz, DMSO) δ = 158.7, 152.1, 151.5, 141.4, 141.3, 133.0, 132.4, 131.0, 128.9, ...
Embodiment 2
[0023] Add 2mg of CuI catalyst, 24mg of o-hydroxybenzonitrile, 22μL of p-methoxyphenylacetylene and 20μL of p-toluenesulfonyl azide into a 10ml reaction tube, then add 1ml of dichloromethane, and drop 40mg of triethylamine dropwise after nitrogen replacement. Add to reaction tube. The reaction mixture was heated at 80°C for 4 h, the mixture was filtered, washed three times with petroleum ether / ethyl acetate (volume ratio 5 / 1, 10 mL), the filtrate was combined and concentrated, and separated by column chromatography, the eluent was petroleum ether / ethyl acetate Ethyl acetate (volume ratio 1 / 1) 600ml to obtain the final product N-[4-amino-3-(4-methoxyphenyl)-benzopyran-2-ylidene]-4-methyl- Benzenesulfonamide, the productive rate is 87%. 1 H NMR(500MHz, DMSO) δ= 8.25 (d, J=10.0 Hz, 1H), 7.81 (d, J=5.0 Hz,2H), 7.70 (t, J=10.0 Hz, 1H), 7.43 (dd, J =5.0, 10.0 Hz, 2H), 7.32 (d, J=10.0Hz, 2H), 7.20 (d, J=10.0 Hz, 2H), 7.06 (d, J=10.0 Hz, 2H), 3.83 (s, 3H ), 2.33(s, 3H); 13 C NMR ...
Embodiment 3
[0025] Add 2mg of CuI catalyst, 24mg of o-hydroxybenzonitrile, 22μL of 3-methoxyphenylacetylene and 20μL of p-toluenesulfonyl azide into a 10ml reaction tube, then add 1ml of dichloromethane, replace with nitrogen and replace with 40mg of triethylamine Add dropwise to the reaction tube. The reaction mixture was heated at 80°C for 4 h, the mixture was filtered, washed three times with petroleum ether / ethyl acetate (volume ratio 5 / 1, 10 mL), the filtrate was combined and concentrated, and separated by column chromatography, the eluent was petroleum ether / ethyl acetate Ethyl acetate (volume ratio 1 / 1) 600ml to obtain the final product N-[4-amino-3-(3-methoxyphenyl)-benzopyran-2-ylidene]-4-methyl- Benzenesulfonamide, the productive rate is 93%. 1 H NMR (500 MHz, CDCl 3 ) δ = 7.86 (d, J=10.0, 2H), 7.79 (d, J=5.0 Hz,1H), 7.47 (t, J=5.0 Hz, 1H), 7.22 (dd, J=10.0, 10.0 Hz, 3H ), 7.14 (dd, J=5.0,5.0 Hz, 2H), 6.70 (dd, J=10.0 10.0 Hz, 3H), 5.97 (s, 2H), 3.63 (s, 3H), 2.34(s, 3H); 1...
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