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Preparation method for substituted isocoumarin derivatives

A technology of isocoumarin and derivatives, applied in organic chemistry and other fields, can solve the problems of low yield, long reaction time, and high requirements for reaction conditions, and achieve the effects of high yield, short reaction time, and strong reaction specificity

Active Publication Date: 2019-08-16
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And the productive rate of the synthetic method of existing substituted isocoumarin derivatives is still low, and reaction condition requirement is high, and reaction time is still longer

Method used

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  • Preparation method for substituted isocoumarin derivatives
  • Preparation method for substituted isocoumarin derivatives
  • Preparation method for substituted isocoumarin derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of 8-methoxy-3-(2-methoxyphenyl)-1H-isochromen-1-one

[0025]

[0026] Add 0.15 mmol of sodium phosphate, 0.005 mmol of p-methylcymene ruthenium (II) dichloride dimer, 0.15 mmol of 2,4,6-trimethylbenzoic acid, 2-(dimethyl (oxo) -λ 6 Sulfanyl)-1-(2-methoxyphenyl)ethan-1-one 0.2mmol, and 1,1,1,3,3,3-hexafluoro-2-propanol 1mL added to 15mL reaction tube, placed in an oil bath at 110°C, and reacted for 24 hours; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Drying, filtration, concentration, and purification by thin-layer chromatography gave 13.2 mg of the target product with a yield of 48%. The NMR and high-resolution mass spectrometry of this compound are characterized as follows: 1 H NMR (500MHz, Chloroform-d) 68.00(d, J=7.7Hz, 1H), 7.61(t, J=8.1Hz, 1H), 7.40-7.36(m, 1H), 7.30(s, 1H), 7.09 -7.03(m, 2H), 7.00(d, J=8.3Hz, 1H), 6.9...

Embodiment 2

[0028] Preparation of 8-phenoxy-3-(2-phenoxyphenyl)-1H-isochromen-1-one

[0029]

[0030] Add 0.15 mmol of sodium phosphate, 0.005 mmol of p-methylcymene ruthenium (II) dichloride dimer, 0.15 mmol of 2,4,6-trimethylbenzoic acid, 2-(dimethyl (oxo) -λ 6 Sulfanyl)-1-(2-phenoxyphenyl)ethan-1-one 0.2mmol, and 1,1,1,3,3,3-hexafluoro-2-propanol 1mL added to 15mL reaction tube, placed in an oil bath at 110°C, and reacted for 24 hours; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Drying, filtration, concentration, and purification by thin-layer chromatography gave 17.3 mg of the target product with a yield of 43%. The NMR and high-resolution mass spectrometry of this compound are characterized as follows: 1 H NMR (500MHz, Chloroform-d) δ8.09-8.06(m, 1H), 7.50(t, J=8.0Hz, 1H), 7.40-7.31(m, 6H), 7.25-7.21(m, 1H), 7.18-7.13(m, 2H), 7.11(d, J=7.7Hz, 1H), 7.0...

Embodiment 3

[0032] Preparation of 8-fluoro-3-(2-fluorophenyl)-1H-isochromen-1-one

[0033]

[0034] Add 0.15 mmol of sodium phosphate, 0.005 mmol of p-methylcymene ruthenium (II) dichloride dimer, 0.15 mmol of 2,4,6-trimethylbenzoic acid, 2-(dimethyl (oxo) -λ 6 Add 0.2mmol of sulfanyl)-1-(2-fluorophenyl)ethan-1-one and 1mL of 1,1,1,3,3,3-hexafluoro-2-propanol into a 15mL reaction tube , placed in an oil bath at 110°C, reacted for 24h; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Drying, filtration, concentration, and purification by thin-layer chromatography gave 17.1 mg of the target product, with a yield of 67%. The NMR and high-resolution mass spectrometry of this compound are characterized as follows: 1 H NMR (500MHz, Chloroform-d) δ8.04-7.99(m, 1H), 7.72-7.67(m, 1H), 7.44-7.39(m, 1H), 7.32-7.26(, 2H), 7.21-7.15( ,3H); 13C NMR (126MHz, Chloroform-d) δ1...

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Abstract

The invention discloses a preparation method for substituted isocoumarin derivatives. The method comprises the following steps: a novel carbon-carbon bond and a carbon-oxygen bond are constructed while a carbon-carbon bond and a carbon-hydrogen bond are cut, a base, dichloro(p-cymene)ruthenium(II) dimer, 2,4,6-trimethylbenzoic acid and sulfur ylide are reacted in an organic solvent, and thereforethe substituted isocoumarin derivatives are prepared. According to the method provided by the invention, the raw materials used in the method are easy to obtain, the yield is high, the reaction conditions are mild, the reaction time is short, the substrate range is wide, the reaction specificity is strong, and the post-treatment is simple and green.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of substituted isocoumarin derivatives. Background technique [0002] Isocoumarin derivatives are one of the basic organic structural units. At the same time, they are widely found in natural products and are also important intermediates in industrial organic synthesis. They are widely used in many fields such as medicine, food flavors, and pesticides. For example, 3-phenylisocoumarin, which has significant antibacterial activity, has obvious drug activity against wheat head blight. 3-(4-bromophenyl)-1H-isobenzopyran-1-one has obvious inhibitory effect on Gram bacteria, and also has inhibitory effect on human, animal and plant pathogens. Therefore, the synthesis of substituted isocoumarin derivatives is one of the important contents of organic chemistry, so the synthesis of substituted isocoumarin derivatives is still a research hotspot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/76
CPCC07D311/76
Inventor 程国林文思
Owner HUAQIAO UNIVERSITY
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