Method for efficiently preparing polysubstituted pyrazole derivative in water phase

A technology of derivatives and pyrazoles, applied in the field of efficient preparation of multi-substituted pyrazole derivatives, achieving high selectivity and yield, and good industrial application prospects

CN114539154APending Publication Date: 2022-05-27HUBEI UNIV OF SCI & TECH
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Authority / Receiving Office
CN · China
Current Assignee / Owner
Publication Date
2022-05-27

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Abstract

The invention provides a method for efficiently preparing polysubstituted pyrazole derivatives in a water phase, and belongs to the technical field of organic synthesis. The method comprises the following steps: adding a proper amount of water, a small amount of solvent and a proper amount of alkali into a container filled with a substituted 2-methylene benzofuranone derivative and a toluenesulfonyl diazomethane derivative, stirring at a proper reaction temperature, filtering after the reaction is finished, adding water or a saturated salt aqueous solution into the filtrate, extracting with an organic solvent, and drying to obtain the substituted 2-methylene benzofuranone derivative. And carrying out reduced pressure distillation and concentration to remove the solvent, and carrying out column chromatography separation on the crude product to obtain the target product polysubstituted pyrazole derivative. The method has the advantages of efficient reaction, environmental protection, convenience, rapidness, wide substrate adaptability, high yield and the like, and has a good industrial application prospect.
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Description

technical field

[0001] The invention belongs to the technical field of organic synthesis, and relates to a method for efficiently preparing polysubstituted pyrazole derivatives in an aqueous phase. Background technique

[0002] Pyrazole skeleton is an important nitrogen heterocyclic skeleton, in addition to its various biological activities, it also has remarkable medicinal properties, including anticancer, antiviral, antibacterial, antifungal, antituberculosis, antiinflammatory, antidiabetic, Antimycobacterial, anesthetic and analgesic properties. Due to their versatile coordination chemistry and photophysical properties, pyrazole-derived ligands have applications in catalysis, metal extraction, and photochemistry. Due to these important applications, it is imperative to develop an efficient synthetic method. The most common methods of pyrazole synthesis include 1,3-dicarbonyl condensation or 1,3-dipolar cycloaddition of α,β-unsaturated aldehydes with hydrazines, and diaz...

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Embodiment Construction

[0023] The following are specific embodiments of the present invention and the accompanying drawings to further describe the technical solutions of the present invention, but the present invention is not limited to these embodiments.

[0024] General method for the synthesis of substituted polysubstituted pyrazole derivatives

[0025] like figure 1 As shown, the synthesis steps of the polysubstituted pyrazole derivatives (I) provided by the present invention are as follows: adding 0.1 mmol of 2-methylene benzofuranone (II) (such as 2-phenylmethylene) into the reaction vessel benzofuranone, etc.), substituted tosyldiazomethane derivatives (III) (eg: 1-phenyltoluenesulfonyldiazomethane derivatives, etc.) 0.12 mmol, base (eg: Cs 2 CO 3 etc.) 2.0mmol, then add 2~3mL mixed solvent (such as: water:acetone=1:2), react at room temperature, add water or saturated salt solution after the reaction, then extract with organic solvent, dry, concentrate under reduced pressure to remove the...