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Green preparation method of water-soluble vitamin E participated isoxazole compound

A technology of alkyne compounds and compounds, which is applied in the field of green synthesis of isoxazole compounds, can solve the problems of excessive waste and large pollution, and achieve the effects of efficient reaction conditions, zero emissions, and mild reaction conditions

Active Publication Date: 2021-11-02
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to solve the problems of large pollution and waste in the prior art, the present invention provides a green and convenient synthesis method of isoxazole compounds represented by formula (Ⅲ), in which the micromicelles formed by TPGS-750-M participate in The synthesis of isoxazole compounds is completed in the water phase. This invention not only has the characteristics of wide applicability of the reaction substrate, but also reduces the use of organic solvents, avoiding the harsh conditions and serious environmental hazards of traditional methods. , has the characteristics of mild reaction conditions, high efficiency, green and environmental protection, responds to the concept of sustainable development, and realizes zero discharge of solvents

Method used

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  • Green preparation method of water-soluble vitamin E participated isoxazole compound
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  • Green preparation method of water-soluble vitamin E participated isoxazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: Synthesis of 3,5-diphenylisoxazole

[0043]

[0044] Add 24.1mg (0.18mmol) NCS, 18.2mg (0.15mmol) benzaldoxime (I-1) in the reaction bottle of 5mL, then add 1mL newly prepared 2wt.% TPGS-750-M aqueous solution in the bottle, The mixture was stirred at room temperature for 4 hours. Four hours later, add 14 μL (0.1 mmol) Et 3 N, 10.2mg (0.1mmol) phenylacetylene (II-1), react at room temperature for 8h. After the reaction, add 2 mL of ethyl acetate to the reaction flask, stir for 5 min, and then let stand to separate layers. After collecting the upper organic phase, add 2 mL of ethyl acetate to the lower aqueous phase, stir for 5 min, and let stand for layering. Collect the upper organic phase. Finally, the organic phases obtained twice were combined, the solvent was evaporated under reduced pressure, the solid residue was separated by column chromatography, the eluent was petroleum ether: ethyl acetate = 1:2, the eluent containing the target product was co...

Embodiment 2

[0047] Example 2: Synthesis of 3,5-diphenylisoxazole

[0048] Add 24.1mg (0.18mmol) NCS, 18.2mg (0.15mmol) benzaldoxime (I-1) in the reaction bottle of 5mL, then add 1mL newly prepared 2wt.% TPGS-750-M aqueous solution in the bottle, The mixture was stirred at room temperature for 4 hours. Four hours later, 7 μL (0.05 mmol) Et was added sequentially 3 N, 10.2mg (0.1mmol) phenylacetylene (II-1), react at room temperature for 14h. After the reaction, add 2 mL of ethyl acetate to the reaction flask, stir for 5 min, and then let stand to separate layers. After collecting the upper organic phase, add 2 mL of ethyl acetate to the lower aqueous phase, stir for 5 min, and let stand for layering. Collect the upper organic phase. Finally, the organic phases obtained twice were combined, the solvent was evaporated under reduced pressure, and the solid residue was separated by column chromatography. The eluent was petroleum ether: ethyl acetate (v / v)=1:2, and the fraction containing the...

Embodiment 3

[0049] Example 3: Synthesis of 3,5-diphenylisoxazole

[0050] Add 24.1mg (0.18mmol) NCS, 18.2mg (0.15mmol) benzaldoxime (I-1) in the reaction bottle of 5mL, then add 1mL newly prepared 2wt.% TPGS-750-M aqueous solution in the bottle, The mixture was stirred at room temperature for 4 hours. After four hours, add 21μL (0.15mmol) Et 3 N, 10.2mg (0.1mmol) phenylacetylene (II-1), reacted at room temperature for 7h. After the reaction, add 2 mL of ethyl acetate to the reaction flask, stir for 5 min, and then let stand to separate layers. After collecting the upper organic phase, add 2 mL of ethyl acetate to the lower aqueous phase, stir for 5 min, and let stand for layering. Collect the upper organic phase. Finally, the organic phases obtained twice were combined, the solvent was evaporated under reduced pressure, the solid residue was separated by column chromatography, the eluent was petroleum ether: ethyl acetate = 1:2, the eluent containing the target product was collected, an...

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Abstract

The invention provides a green synthesis method of an isoxazole compound as shown in a formula (III). The method comprises the following steps: by taking an aldoxime compound as shown in a formula (I) as a substrate, reacting with an alkyne compound as shown in a formula (II) at room temperature for 6-16 hours in an aqueous solution of a surfactant with the mass concentration of 1wt%-5wt% under the combined action of N-chlorosuccinimide and an alkaline substance, and carrying out post-treatment on the obtained reaction liquid to obtain the isoxazole compound as shown in the formula (III). According to the invention, water is used as a reaction solvent, so the usage amount of an organic solvent is reduced, and zero emission of the solvent is realized.

Description

technical field [0001] The invention relates to a green synthesis method of isoxazole compounds participated by water-soluble vitamin E. Background technique [0002] Isoxazoles are common structural backbones in many bioactive molecules. Isoxazole derivatives also have a wide range of biological activities, such as neurotoxins (A), antidepressant-like active substances (B), anti-β-lactamase antibiotics (C), and synthetic androgen danazol (D) Probe with histone deacetylase (HADC) that inhibits gonadotropin production (E). In addition, isoxazole derivatives can also be used as the main precursors for the synthesis of different organic compounds. [0003] [0004] Several methods are currently available for the synthesis of isoxazole scaffolds. In 2005, Fokin's research group used sodium ascorbate to convert CuSO 4 ·5H 2 The reduction of O to Cu(I) was used as a catalyst to catalyze the formation of isoxazole derivatives from N-hydroxyimidyl chloride and alkynes. The ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D261/08C07D413/04C07D261/18
CPCC07D261/08C07D413/04C07D261/18
Inventor 王宇光周金秋刘贝陈圆
Owner ZHEJIANG UNIV OF TECH
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