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Preparation method for 2,3-disubstituted benzo-gamma-pyrone derivative

A technology of pyrone and disubstitution, applied in 2 fields, can solve the problems of low efficiency, not enough environmental protection, cumbersome steps, etc., and achieve the effect of moderate reaction time, mild reaction conditions and wide substrate range

Active Publication Date: 2019-09-20
HUAQIAO UNIVERSITY
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Problems solved by technology

Its core structure has potential medicinal value, but the method for synthesizing multi-substituted chromones in the prior art still has the problems of low efficiency, cumbersome steps and not being environmentally friendly enough, so it is of great significance to develop an efficient, green and concise method for synthesizing multi-substituted chromones important meaning

Method used

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  • Preparation method for 2,3-disubstituted benzo-gamma-pyrone derivative
  • Preparation method for 2,3-disubstituted benzo-gamma-pyrone derivative
  • Preparation method for 2,3-disubstituted benzo-gamma-pyrone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 3-(6-methylquinolin-2-yl)-2-phenyl-4H-chromen-4-one

[0027]

[0028] Add 0.1mmol of the corresponding substituted alkyne ketone, 0.2mmol of 3-methylquinoline 1-oxide, 0.3mmol of sodium phosphate, and 0.5mL of N,N-dimethylformamide into a 15mL reaction tube, and place at 100°C In an oil bath, react under air atmosphere for 12h; cool to room temperature, dilute the reaction solution with ethyl acetate, wash with water three times, 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 of this target product are characterized 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 )δ 177.3, 163.2, 156.1, ...

Embodiment 2

[0030] 3-(6-Bromoquinolin-2-yne)-2-phenyl-4H-chromen-4-one

[0031]

[0032] Add 0.1mmol of the corresponding substituted alkyne ketone, 0.2mmol of 3-bromoquinoline 1-oxide, 0.3mmol of sodium phosphate, and 0.5mL of N,N-dimethylformamide into a 15mL reaction tube, and place in a 100°C In an oil bath, react under an air atmosphere for 12 h; cool to room temperature, dilute the reaction solution with ethyl acetate, wash three times with water, and remove the organic phase with Na 2 SO 4 Dry, filter, concentrate, and purify by column chromatography to obtain 26.7 mg of the target product with a yield of 63%. The NMR and high-resolution mass spectrometry of this target product are characterized 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, 156.1, 154.1, ...

Embodiment 3

[0034] 3-(5-Bromoisoquinolin-1-yl)-2-phenyl-4H-chromen-4-one

[0035]

[0036] Add 0.1mmol of the corresponding substituted alkyne ketone, 0.2mmol of 5-bromoisoquinoline 2-oxide, 0.3mmol of sodium phosphate, and 0.5mL of N,N-dimethylformamide into a 15mL reaction tube, and place at 100°C In an oil bath, react under air atmosphere for 12h; cool to room temperature, dilute the reaction solution with ethyl acetate, wash with water three times, organic phase Na 2 SO 4 Dry, filter, concentrate, and purify by column chromatography to obtain 18.1 mg of the target product with a yield of 43%. The NMR and high-resolution mass spectrometry of this target product are characterized 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 )δ 177.2, 163.5, 156.3, ...

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Abstract

The invention discloses a preparation method for a 2,3-disubstituted benzo-gamma-pyrone derivative. The 2,3-disubstituted benzo-gamma-pyrone derivative is prepared by one-step reaction of substituted alkynone with quinoline oxynitride; the reaction process comprises intermolecular regioselective 1,3-dipolar cycloaddition, an N-O bond cleavage reaction and then molecular oxyarylation; so the 2,3-disubstituted benzo-gamma-pyrone derivative is prepared through the one-pot method. The method of the invention has the advantages of easy availability of raw materials, high yield, mild reaction conditions, moderate reaction time, wide substrate scope, strong reaction specificity, simple post-treatment and environmental friendliness.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 2,3-disubstituted benzo-γ-pyrone derivatives. Background technique [0002] Natural products with chromone as the main skeleton have a wide range of biological activities. For example, it is used as a fungicide, an antioxidant, and some derivatives have been used to treat rhinitis and bronchial diseases due to their remarkable biological characteristics. Its core structure has potential medicinal value, but the method for synthesizing multi-substituted chromones in the prior art still has the problems of low efficiency, cumbersome steps and not being environmentally friendly enough, so it is of great significance to develop an efficient, green and concise method for synthesizing multi-substituted chromones important meaning. Contents of the invention [0003] The purpose of the present invention is to overcome the defects of the p...

Claims

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Application Information

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IPC IPC(8): C07D405/04C07D409/14
CPCC07D405/04C07D409/14
Inventor 程国林刘景
Owner HUAQIAO UNIVERSITY
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