A kind of preparation method of 2,3-disubstituted benzo-γ-pyrone derivatives
A technology of pyrone and disubstitution, applied in 2 fields, can solve the problems of not being environmentally friendly, cumbersome steps, low efficiency, etc., and achieve the effects of moderate reaction time, wide substrate range, and simple post-treatment
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0026] 3-(6Methylquinolin-2-yl)-2-phenyl-4H-chromen-4-one
[0027]
[0028] The corresponding substituted alkynone 0.1mmol, 3-methylquinoline 1-oxide 0.2mmol, sodium phosphate 0.3mmol, N,N-dimethylformamide 0.5mL were added to a 15mL reaction tube, placed at 100 ℃ In the oil bath of , react under air atmosphere for 12h; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed with water three times, the organic phase Na 2 SO 4 Dry, filter, concentrate, and purify by column chromatography to obtain 32.8 mg of the target product with a yield of 90%. The NMR and high-resolution mass spectrometry characterizations of the target product are as follows: 1 H NMR (500MHz, CDCl 3 )δ8.22 (m, J=8.0, 1.7Hz, 1H), 7.97 (d, J=8.4Hz, 1H), 7.76 (d, J=8.6Hz, 1H), 7.63 (m, J=8.7, 7.2 , 1.7Hz, 1H), 7.48(m, 2H), 7.39(m, J=8.6, 1.9Hz, 1H), 7.36(d, J=8.3Hz, 2H), 7.33(m, 2H), 7.19(m , 1H), 7.11 (m, 2H), 2.44 (s, 3H); 13 C NMR (126MHz, CDCl 3 )δ177.3, 163.2, 1...
Embodiment 2
[0030] 3-(6-Bromoquinolin-2-yn)-2-phenyl-4H-chromen-4-one
[0031]
[0032] The corresponding substituted alkynone 0.1mmol, 3-bromoquinoline 1-oxide 0.2mmol, sodium phosphate 0.3mmol, N,N-dimethylformamide 0.5mL were added to a 15mL reaction tube, placed in a 100 ℃ In an oil bath, the reaction was carried out in an air atmosphere for 12 h; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase Na 2 SO 4 It was dried, filtered, concentrated, and purified by column chromatography to obtain 26.7 mg of the target product with a yield of 63%. The NMR and high-resolution mass spectrometry characterizations of the target product are as follows: 1 H NMR (500MHz, CDCl 3 )δ8.23(m, 1H), 7.98(d, J=8.4Hz, 1H), 7.89(d, J=2.1Hz, 1H), 7.72(d, J=9.0Hz, 1H), 7.64(m, 2H), 7.50(d, J=8.4Hz, 1H), 7.44(d, J=8.5Hz, 1H), 7.38(m, 1H), 7.31(m, 2H), 7.22(m, 1H), 7.13( m, 2H); 13 C NMR (126MHz, CDCl 3 )δ177.2, 163.5,...
Embodiment 3
[0034] 3-(5-Bromoisoquinolin-1-yl)-2-phenyl-4H-chromen-4-one
[0035]
[0036] The corresponding substituted alkynone 0.1mmol, 5-bromoisoquinoline 2-oxide 0.2mmol, sodium phosphate 0.3mmol, N,N-dimethylformamide 0.5mL were added to a 15mL reaction tube, placed at 100 ℃ In the oil bath of , react under air atmosphere for 12h; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed with water three times, the organic phase Na 2 SO 4 It was dried, filtered, concentrated, and purified by column chromatography to obtain 18.1 mg of the target product with a yield of 43%. The NMR and high-resolution mass spectrometry characterizations of the target product are as follows: 1 H NMR (500MHz, CDCl 3 )δ8.54(d, J=5.9Hz, 1H), 8.21(m, 1H), 7.93(d, J=5.9Hz, 1H), 7.86(d, J=7.4Hz, 1H), 7.80(d, J=8.3Hz, 1H), 7.69(m, 1H), 7.55(d, J=8.4Hz, 1H), 7.40(t, J=7.5Hz, 1H), 7.25(m, 3H), 7.19(d, J=6.4Hz, 1H), 7.09 (t, J=7.7Hz, 2H); 13 C NMR (126MHz, CDCl 3 )δ177.2...
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More