Synthesis method of C-3 alkyl substituted coumarin derivative

A technology of a coumarin derivative and a synthesis method, which is applied in the field of synthesis of C-3-position alkyl substituted coumarin derivatives, can solve the problems of high reaction temperature, harsh conditions, inapplicability and the like, and achieves good reaction selectivity , The effect of safe reaction and easy operation

Active Publication Date: 2019-05-17
ZHEJIANG UNIV OF TECH
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AI Technical Summary

Problems solved by technology

The above-mentioned method of coumarin C-3 functionalization often requires higher reaction temperature, harsh conditions, and large energy consumption.
In addition, the existing methods can only introduce aryl, alkenyl, cycloalkyl and ether free radicals on coumarin C-3, but are not suitable for the more difficult saturated straight-chain alkyl groups. certain limitations

Method used

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  • Synthesis method of C-3 alkyl substituted coumarin derivative
  • Synthesis method of C-3 alkyl substituted coumarin derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Coumarin (0.5mmol, 73mg), N-(2,2-dimethyl)propionyloxyphthalimide (1.0mmol, 247mg), Ir(ppy) 3 (0.01 mmol, 6.5 mg) and trifluoroacetic acid (0.25 mmol, 28.5 mg) were added to a 5 mL single-neck reaction flask, DMSO (1.0 mL) was added as a solvent, under N 2 Under the protection of the atmosphere, the reaction was carried out under the irradiation of 3w white light and the temperature of 25°C for 24h. After the reaction, the reaction system was washed with water and extracted with dichloromethane, and the organic layer and the water layer were separated. After the organic layer was dried with anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to remove the solvent to obtain a yellow oil. The yellow oil was separated by column chromatography, using a mixture of petroleum ether and ethyl acetate with a volume ratio of 30:1 as the eluent, the eluent containing the target compound was collected, the solvent was evaporated and dried to obtain 81.9 mg o...

Embodiment 2

[0029] The protic acid (trifluoroacetic acid) in the system was replaced with trifluoromethanesulfonic acid (0.25mmol, 37.5mg), and other operations were the same as in Example 1 to obtain 76mg white solid 3-tert-butyl coumarin, yield 75% .

Embodiment 3

[0031] The N-(2,2-dimethyl) propionyloxy phthalimide feeding amount was changed to 0.5 mmol, and other operations were the same as in Example 1 to obtain 58 mg of white solid 3-tert-butyl coumarin, Yield 57%.

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Abstract

The invention discloses a synthesis method of a C-3 alkyl substituted coumarin derivative. The synthesis method comprises the following steps: dissolving a coumarin derivative shown as a formula (I),an N-alkyloxyphthalimide compound shown as a formula (II), a photocatalyst and a proton acid in an organic solvent; reacting under visible light irradiation at a temperature of 20 to 60 DEG C for 3 to36 hours; after the reaction is finished, performing post-treatment on a reaction system to obtain a target product of the C-3 alkyl substituted coumarin derivative shown as a formula (III), whereinthe reaction formulas are shown in the description; in the formulas (I) and the formula (III), the substituent R1 is H, methyl, methoxy, fluorine, chlorine or bromine; in the formula (II) and the formula (III), the substituent R2 is linear alkyl or naphthenic alkyl of with 1 to 8 carbon atoms. The synthesis method realizes the C-3alkylation of coumarin with light as reaction energy, makes the reaction safer, more environmentally friendly and cheaper, expands the application range of the reaction substrate, and enriches the synthesis method of a C-3 substituted coumarin compound.

Description

technical field [0001] The invention relates to a method for synthesizing a C-3-position alkyl substituted coumarin derivative. Background technique [0002] Coumarin derivatives are an important class of natural compounds that widely exist in the plant kingdom. Studies have shown that coumarin compounds have good biological activity, and have significant effects in antibacterial, anti-inflammatory, anti-cancer, and anti-HIV virus, and have a wide range of applications in the field of medicine. In addition, the good optical properties of coumarins also make them have an important position in the field of organic optical materials. In recent years, the synthesis of 3-substituted coumarin derivatives has received extensive attention, and some progress has been made. [0003] The existing 3-position substituted coumarin derivatives synthesis methods mainly include the following: obtain alkylated coumarin by two-component or multi-component ring formation, and catalyze the cou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/12C07D311/14C07D311/16C07D311/18
Inventor 孙彬金灿颜志阳
Owner ZHEJIANG UNIV OF TECH
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