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Synthesis method of 4-allyl-3,5-disubstituted isooxazole

A synthetic method and a two-substitution technology, which is applied in the field of isoxazole preparation, can solve the problems of harsh reaction conditions, low atom utilization rate, and low reaction yield, and achieve the effects of short reaction time, high yield, and easy availability of raw materials

Active Publication Date: 2018-11-23
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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  • Synthesis method of 4-allyl-3,5-disubstituted isooxazole
  • Synthesis method of 4-allyl-3,5-disubstituted isooxazole
  • Synthesis method of 4-allyl-3,5-disubstituted isooxazole

Examples

Experimental program
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Effect test

Embodiment 1

[0053] Add 0.025 mmol Pd(OAc) to the test tube 2 , 0.5 mmol n-butyl ammonium bromide, 0.5 mmol acetylene ketoxime ether (R 1 = R 2 =Ph) and 0.75 mmoles of 3-bromopropene, finally add 1.0 milliliter of N,N-dimethylformamide (DMF) at 600 rpm, stir the reaction at 80°C, detect the reaction by TLC, stop stirring after the reaction is complete, and cool to Add 3 mL of saturated ammonium chloride solution prepared in advance at room temperature, and then add ethyl acetate to extract 3 times to combine the organic phase, and 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 developing solvents (PE:EA=200:1), separated by thin-layer plates to obtain the final target product, and the separation yield was 99%. The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows figure 1 with figure 2shown; the struct...

Embodiment 2

[0061] Add 0.025 mmol Pd(OAc) to the test tube 2 , 0.5 mmol n-butyl ammonium bromide, 0.5 mmol acetylene ketoxime ether (R 1 =Ph,R 2 =4-MePh) and 0.75 mmoles of 3-bromopropene, finally add 1.0 milliliter of N,N-dimethylformamide (DMF) at 600 rpm, stir the reaction at 80°C, detect the reaction by TLC, stop stirring after the reaction is complete, Cool to room temperature and add 3 mL of saturated ammonium chloride solution prepared in advance, then add ethyl acetate to extract 3 times to combine the organic phase, and 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 developing solvents (PE:EA=200:1), separated by thin-layer plates to obtain the final target product, and the separation yield was 99%. The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows image 3 with Figure 4 shown; the struct...

Embodiment 3

[0068] Add 0.025 mmol Pd(OAc) to the test tube 2 , 0.5 mmol n-butyl ammonium bromide, 0.5 mmol acetylene ketoxime ether (R 1 =3,4-diMeOPh,R 2 =Ph) and 0.75 mmoles of 3-bromopropene, finally add 1.0 milliliter of N,N-dimethylformamide (DMF) at 600 rpm, stir the reaction at 80°C, detect the reaction by TLC, stop stirring after the reaction is complete, and cool to Add 3 mL of saturated ammonium chloride solution prepared in advance at room temperature, and then add ethyl acetate to extract 3 times to combine the organic phases, and 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 developing solvents (PE:EA=200:1), separated by thin-layer plates to obtain the final target product, and the separation yield was 98%. The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows Figure 4 with Image 6 show...

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Abstract

The invention discloses a synthesis method of 4-allyl-3,5-disubstituted isooxazole, and belongs to the technical field of organic synthesis. The synthesis method is characterized in that in a reactor,acetyenic ketone oxime ether substrates, 3-bromopropylene, palladium catalysts, additives and solvents are added; stirring reaction is performed at 70 to 80 DEG C; a reaction product is separated andpurified to obtain the 4-allyl-3,5-disubstituted isooxazole. The method has the advantages that a product obtained by performing Sonogashira coupling on simple and easy-to-obtain acyl chloride and alkyne, and methoxylamine hydrochloride react to obtain a series of norethisteroneoxime ether; the reaction conditions are mild; no environment pollution exists; a potential functional 4-allyl-3,5-disubstituted isooxazole compound is built. The method has innovativeness and atom economy; the conditions are mild; the operation is safe; the scale can be magnified to 5g level scale without influencingthe yield, so that potential practical values are realized.

Description

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

Claims

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Application Information

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Patent Type & Authority Applications(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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