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A kind of synthetic method of 4-allyl-3,5-disubstituted isoxazole

A synthetic method and a disubstitution technology, applied in the field of isoxazole preparation, can solve the problems of low atom utilization rate, low reaction yield, harsh reaction conditions, etc., and achieve the effects of short reaction time, easy availability of raw materials, and mild conditions

Active Publication Date: 2022-05-24
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Literature research found that these methods also have corresponding limitations. For example, the strategy of C-H activation often requires the introduction of directing groups and is accompanied by disadvantages such as harsh reaction conditions; low reaction yield and low atom utilization.

Method used

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  • A kind of synthetic method of 4-allyl-3,5-disubstituted isoxazole
  • A kind of synthetic method of 4-allyl-3,5-disubstituted isoxazole
  • A kind of synthetic method of 4-allyl-3,5-disubstituted isoxazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Add 0.025 mmol Pd(OAc) to the test tube 2 , 0.5 mmol n-butylammonium bromide, 0.5 mmol alkynone oxime ether (R 1 =R 2 = Ph) and 0.75 mmol of 3-bromopropene, finally add 1.0 ml of N,N-dimethylformamide (DMF) at 600 rpm rotating speed, stir the reaction at 80 ° C, detect the reaction by TLC, stop stirring after the reaction is completed, and cool to Add 3 mL of pre-prepared saturated ammonium chloride solution at room temperature, and then add ethyl acetate to extract 3 times, combine the organic phases, use anhydrous MgSO 4 Drying, filtration, and rotary evaporation under reduced pressure to remove the solvent, using petroleum ether (PE) and ethyl acetate (EA) as the developing solvent (PE:EA=200:1), the final target product was obtained by thin-layer plate separation, and the separation yield was is 99%. The hydrogen spectrogram and carbon spectrogram of the product obtained in this example are respectively as follows figure 1 and figure 2shown; the structural cha...

Embodiment 2

[0061] Add 0.025 mmol Pd(OAc) to the test tube 2 , 0.5 mmol n-butylammonium bromide, 0.5 mmol alkynone oxime ether (R 1 =Ph,R 2 = 4-MePh) and 0.75 mmol of 3-bromopropene, finally add 1.0 ml of N,N-dimethylformamide (DMF) at 600 rpm rotating speed, stir the reaction at 80 ° C, detect the reaction by TLC, stop stirring after the reaction is complete, Cool to room temperature, add 3 mL of pre-prepared saturated ammonium chloride solution, then add ethyl acetate and extract 3 times, combine the organic phases, use anhydrous MgSO 4 Drying, filtration, and rotary evaporation under reduced pressure to remove the solvent, using petroleum ether (PE) and ethyl acetate (EA) as the developing solvent (PE:EA=200:1), the final target product was obtained by thin-layer plate separation, and the separation yield was is 99%. The hydrogen spectrogram and carbon spectrogram of the product obtained in this example are respectively as follows image 3 and Figure 4 shown; the structural chara...

Embodiment 3

[0068] Add 0.025 mmol Pd(OAc) to the test tube 2 , 0.5 mmol n-butylammonium bromide, 0.5 mmol alkynone oxime ether (R 1 =3,4-diMeOPh,R 2 = Ph) and 0.75 mmol of 3-bromopropene, and finally added 1.0 ml of N,N-dimethylformamide (DMF) at 600 rpm, stirring the reaction at 80 °C, and detecting the reaction by TLC. Add 3 mL of pre-prepared saturated ammonium chloride solution at room temperature, and then add ethyl acetate to extract 3 times, combine the organic phases, use anhydrous MgSO 4 Drying, filtration, and rotary evaporation under reduced pressure to remove the solvent, using petroleum ether (PE) and ethyl acetate (EA) as the developing solvent (PE:EA=200:1), the final target product was obtained by thin-layer plate separation, and the separation yield was is 98%. The hydrogen spectrogram and carbon spectrogram of the product obtained in this example are respectively as follows Figure 5 and Image 6 shown; the structural characterization data is as follows:

[0069] ...

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Abstract

The invention discloses a synthesis method of 4-allyl-3,5-disubstituted isoxazole, belonging to the technical field of organic synthesis. The synthesis method is as follows: in the reactor, add acetylene ketoxime ether substrate, 3-bromopropene, palladium catalyst, additive and solvent, stir and react at 70-80°C, and the reaction product is separated and purified to obtain 4-allyl -3,5-disubstituted isoxazoles. In the method of the present invention, a series of acetylenic ketone oxime ethers are obtained by reacting the product obtained through Sonogashira coupling of simple and easy-to-obtain acyl chlorides and alkynes with methoxyamine hydrochloride, the reaction conditions are mild, and there is no pollution to the environment. Potentially functional 4-allyl-3,5-disubstituted isoxazole compounds, the method is innovative and atom-economical, mild conditions, safe operation, and can be scaled up to 5 g scale without affecting the yield Therefore, it has potential practical value.

Description

technical field [0001] The invention belongs to the field of isoxazole preparation, in particular to a method for synthesizing 4-allyl-3,5-disubstituted isoxazole. Background technique [0002] Isoxazole structures are widely found in natural products and drug molecules. In many drug molecules containing isoxazole skeletons, it is precisely because of the existence of this five-membered heterocyclic structure with N, O atoms that it exhibits important physiological activities. Such as antibacterial, anti-inflammatory, anti-cancer, etc., so the synthesis of this type of compounds has received extensive attention. So far, the construction of isoxazole frameworks is mainly through (1) transition metal-catalyzed [3+2] cycloaddition; (2) cycloaddition using pre-functionalized dipoles as reaction substrates reaction; (3) cycloisomerization strategy and other methods to synthesize. Although these strategies are diverse, there are still some limitations, such as harsh reaction con...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D261/08C07D413/04
CPCC07D261/08C07D413/04
Inventor 伍婉卿李灿李建晓江焕峰
Owner SOUTH CHINA UNIV OF TECH
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