A kind of synthetic method of C-3 alkyl substituted coumarin derivatives

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: 2021-02-19
ZHEJIANG UNIV OF TECH
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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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  • A kind of synthetic method of C-3 alkyl substituted coumarin derivatives
  • A kind of synthetic method of C-3 alkyl substituted coumarin derivatives
  • A kind of synthetic method of C-3 alkyl substituted coumarin derivatives

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Coumarin (0.5mmol, 73mg), N-(2,2-dimethyl)propionyloxyphthalimide (1.0mmol, 247mg), Ir(ppy) 3 (0.01mmol, 6.5mg) and trifluoroacetic acid (0.25mmol, 28.5mg) were added to a 5mL single-port reaction flask, DMSO (1.0mL) was added as a solvent, and the 2 Under the protection of the atmosphere, the reaction was performed under 3w white light irradiation and a temperature of 25°C for 24h. After the reaction, the reaction system was washed with water and extracted with dichloromethane, then separated into an organic layer and an aqueous layer. After the organic layer was dried with anhydrous sodium sulfate, it was evaporated and concentrated 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, collecting the eluate containing the target compound, distilling off the solvent and drying to obtain 81.9 mg of white cr...

Embodiment 2

[0030] The protonic acid (trifluoroacetic acid) in the system was replaced with trifluoromethanesulfonic acid (0.25mmol, 37.5mg), and the other operations were the same as in Example 1 to obtain 76mg of white solid 3-tert-butylcoumarin with a yield of 75% .

Embodiment 3

[0032] N-(2,2-dimethyl) propionyloxyphthalimide charging amount is changed into 0.5mmol, other operation is the same as embodiment 1, obtains 58mg white solid 3-tert-butyl coumarin, Yield 57%.

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Abstract

The invention discloses a synthesis method of C-3 alkyl-substituted coumarin derivatives, which combines the coumarin derivatives represented by the formula (I), the coumarin derivatives represented by the formula (II) N ‑alkanoyloxyphthalimide compound, photocatalyst and protonic acid are dissolved in an organic solvent, and reacted at 20‑60°C for 3‑36 h under visible light irradiation. After the reaction, the reaction system After post-processing, the C-3 alkyl-substituted coumarin derivative target product shown in formula (III) is obtained; the reaction formula is as follows: In formula (I) and formula (III), the substituent R 1 Is H, methyl, methoxy, fluorine, chlorine or bromine; in formula (II) and formula (III), substituent R 2 It is C1-C8 linear alkyl or cycloalkyl. The invention realizes the C-3 alkylation of coumarin by using light as the reaction energy, makes the reaction safer, greener, and lower in cost, expands the scope of application of the substrate of the reaction, and enriches the coumarins substituted by C-3 Compound synthesis method.

Description

technical field [0001] The invention relates to a synthesis method of C-3 alkyl-substituted coumarin derivatives. 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 viruses, and are widely used in the field of medicine. In addition, the good optical properties of coumarin compounds also make them play an important role 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: the coumarin is obtained by forming a ring with two or more components, and the coumarin is catalyzed by metal palladium in ...

Claims

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Application Information

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Patent Type & Authority Patents(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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