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Synthetic method of visible accelerant C-3-site aryl-seleno substituent coumarin

A synthetic method, visible light technology, applied in the direction of organic chemistry, etc., to achieve the effects of low environmental pollution, high yield, and mild reaction conditions

Active Publication Date: 2018-12-21
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the method of constructing C-3 aryl selenyl substituted coumarin has not been reported yet

Method used

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  • Synthetic method of visible accelerant C-3-site aryl-seleno substituent coumarin
  • Synthetic method of visible accelerant C-3-site aryl-seleno substituent coumarin
  • Synthetic method of visible accelerant C-3-site aryl-seleno substituent coumarin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046]

[0047] At room temperature, ammonium peroxodisulfate (0.4 mmol), C-4 aniline substituted coumarin (0.2 mmol), diphenyl Diselenide (0.15 mmol), acetonitrile (2 ml), and a 12-watt blue LED lamp were placed 3 cm away from the reaction tube, and reacted at room temperature for 24 h. The progress of the reaction was monitored by TLC (Thin Layer Chromatography). After the reaction was completed, the resulting solution was cooled to room temperature, and the organic phase was removed from the solvent by a rotary evaporator. The residue was purified with a silica gel column (silica gel specification: 200-300 mesh, eluent: petroleum ether / ethyl acetate (10:1, v / v)) to obtain 63 mg of the target product with a yield of 75%.

[0048] The obtained product nuclear magnetic spectrum data are: 1 H NMR (CDCl 3 ,500MHz,ppm)δ7.88(s,br,1H),7.47-7.44(m,3H),7.35(d,1H,J=8.3Hz),7.31(dd,2H,J=7.6Hz,8.0Hz ),7.24-7.18(m,5H),7.00(d,2H,J=8.0Hz),6.93(t,1H,J=7.3Hz).

[0049] 13 C NMR (CDCl...

Embodiment 2

[0052]

[0053] At room temperature, ammonium peroxodisulfate (0.4 mmol), C-4 aniline substituted coumarin (0.2 mmol), diaryl Diselenide (0.15 mmol), acetonitrile (2 ml), and a 12-watt blue LED lamp were placed 3 cm away from the reaction tube, and reacted at room temperature for 24 h. The progress of the reaction was monitored by TLC (Thin Layer Chromatography). After the reaction was completed, the resulting solution was cooled to room temperature, and the organic phase was removed from the solvent by a rotary evaporator. The residue was purified with a silica gel column (silica gel specification: 200-300 mesh, eluent: petroleum ether / ethyl acetate (15:1, v / v)) to obtain 61 mg of the target product with a yield of 76%.

[0054] The obtained product nuclear magnetic spectrum data are: 1 H NMR (CDCl 3 ,500MHz,ppm)δ7.85(s,br,1H),7.45(t,1H,J=8.2Hz),7.35-7.24(m,5H),7.21-7.18(m,2H),7.10(t, 1H, J=7.6Hz), 7.00-6.98(m, 3H), 6.93(t, 1H, J=8.3Hz), 2.24(s, 3H).

[0055] 13 C NM...

Embodiment 3

[0058]

[0059] At room temperature, add ammonium peroxodisulfate (0.2 mmol), sodium peroxodisulfate (0.3 mmol), C-4 aniline substituted coumarin into a 25 ml Schlenk tube equipped with a magnetic stirrer Chlorine (0.2 mmol), diaryldiselenide (0.2 mmol), 1,2-dichloroethane (2 ml), a 12-watt blue LED lamp placed 3 cm away from the reaction tube, at room temperature Reaction 24h. The progress of the reaction was monitored by TLC (Thin Layer Chromatography). After the reaction was completed, the resulting solution was cooled to room temperature, and the organic phase was removed from the solvent by a rotary evaporator. The residue was purified with a silica gel column (silica gel specifications: 200-300 mesh, eluent: petroleum ether / ethyl acetate (15:1, v / v)) to obtain 65 mg of the target product with a yield of 76%.

[0060] The obtained product nuclear magnetic spectrum data are: 1 H NMR (CDCl 3 ,500MHz,ppm)δ7.85(s,br,1H),7.48(t,1H,J=7.0Hz),7.39-7.31(m,5H),7.23(d,1H,J=7....

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Abstract

The invention discloses a C-3-site aryl-seleno substituent coumarin compound and a preparation method thereof, and a novel method for establishing C-3-site aryl-seleno substituent coumarin by directlyperforming selenium modification on a substituent coumarin C-3-site C-H bond under a visible accelerant condition. The method comprises the following steps: firstly dissolving C-4-site arylamine substituent coumarin compound and diaryl diseleno ether compound in an organic solvent, then adding an oxidant persulfate, magnetically stirring and reacting for 18 to 30 hours under an air and room temperature condition and the illumination of a blue LED light source; and after the reaction is ended, removing the solvent of a reaction solution by virtue of a rotary evaporator, purifying a residue byusing a silica gel column, and preparing the C-3-site aryl-seleno substituent coumarin compound of a general formula (I).

Description

technical field [0001] The invention relates to a method for synthesizing and preparing coumarin compounds substituted by C-3 aromatic selenyl groups, belonging to the field of organic chemistry. Background technique [0002] Coumarin and its derivatives have a variety of biological activities, such as antibacterial and antiproliferative properties; in addition, derivatives based on the core skeleton of coumarin also have anticoagulant, anticancer, anti-HIV, and viral protease Inhibition, estrogen-like effects, central nervous system regulation, photosensitization, etc., have been continuously developed and utilized in various fields. Importantly, compounds containing coumarin skeletons are also commonly found in marketed drug molecules, showing their great application potential. [0003] On the other hand, organoselenium compounds widely exist in natural products and organic molecules with biological activity. Therefore, the development of novel and efficient methods for ...

Claims

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Application Information

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IPC IPC(8): C07D311/12C07D311/16
CPCC07D311/12C07D311/16
Inventor 杨道山厉国庆魏伟
Owner QINGDAO UNIV OF SCI & TECH
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