Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of preparation method of 3-(1h-pyrazol-1-yl) ethyl acrylate compound

A technology of ethyl acrylate and ethyl propionate, applied in organic chemistry, chemical recycling and other directions, can solve the problems of poor substrate applicability, large amount of catalyst, difficult preparation of raw materials, etc., and achieves the realization of reaction conditions, simple and convenient ligand synthesis, The effect of easy reaction conditions

Active Publication Date: 2022-08-09
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI +1
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods usually have shortcomings such as large amount of catalyst used, harsh reaction conditions, difficult preparation of raw materials, and poor substrate applicability.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of preparation method of 3-(1h-pyrazol-1-yl) ethyl acrylate compound
  • A kind of preparation method of 3-(1h-pyrazol-1-yl) ethyl acrylate compound
  • A kind of preparation method of 3-(1h-pyrazol-1-yl) ethyl acrylate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1: CuI and L-1-1 complexed as catalyst to catalyze the reaction to generate (Z)-3-phenyl-3-(3-phenyl-1H-pyrazol-1-yl) ethyl acrylate product III -1.

[0053] The metal precursor CuI (0.01 mmol, 5 mol %) and ligand L-1-1 (0.011 mmol, 5.5 mol %) were added to the reaction flask, 1.0 mL of anhydrous methanol was added under nitrogen protection, and the mixture was stirred at room temperature for 1 hour. Then 3-(2-p-toluenesulfonylhydrazono) propionic acid ethyl ester compound I-1 (0.2 mmol, 1.0 equiv), propargyl alcohol ester II-1 (0.3 mmol, 1.5 equiv) and i Pr 2 NEt (0.24 mmol, 1.2 equiv) was dissolved in 2.0 mL of anhydrous methanol, then the solution was added to the above stirred catalyst solution under nitrogen protection, and the reaction was stirred at 65° C. for 24 h. After the reaction was completed, it was concentrated under reduced pressure until almost solvent-free, separated by silica gel column chromatography, concentrated under reduced pressure, an...

Embodiment 2

[0057] Example 2: L-1-2 reacts as a ligand to generate product III-1

[0058] The ligand L-1-1 in Example 1 was replaced with the ligand L-1-2, the temperature was room temperature, and the rest were the same as those in Example 1. The reaction gave compound III-1 in 30% yield.

[0059] The structural formula of L-1-2 is as follows:

[0060]

Embodiment 3

[0061] Example 3: CuF 2 Catalytic reaction with L-1-1 to produce product III-1

[0062] CuI in Example 1 was used CuF 2 Instead, the temperature is room temperature, and the rest are the same as in Example 1. Compound III-1 was obtained in 35% yield.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a preparation method of 3-(1H-pyrazole-1-yl) ethyl acrylate compound, which adopts copper catalyst to catalyze 3-(2-p-toluenesulfonimide) ethyl propionate A method for preparing a series of 3-(1H-pyrazole-1-yl) ethyl acrylate compounds by the [2+3] cycloaddition reaction of a compound and a propargyl compound. The reaction uses the metal complexes generated in situ between CuI and pyridinebisoxazoline ligands as catalysts, and can be carried out at 65°C with methanol, tetrahydrofuran, etc. as solvents. The present invention has the characteristics of relatively mild reaction conditions, easy availability of raw materials, high regioselectivity, wide substrate adaptation range and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a [2+3] cycloaddition reaction of a copper-catalyzed ethyl 3-(2-p-toluenesulfonimidyl) propionate compound and a propargyl compound. A regioselective method for the preparation of a series of ethyl 3-(1H-pyrazol-1-yl)acrylates. Background technique [0002] The synthesis and application of heterocyclic compounds has always been one of the research hotspots and frontiers of organic synthetic chemistry. As an important class of heterocyclic compounds, pyrazole derivatives have attracted more and more attention due to their wide range of biological activities. [(a) Aiello E, Aiello S, Mingoia F, Synthesis and antimicrobial activity of new 3-(1-R-3(5)–methyl-4-nitroso-1H-5(3)-pyrazolyl)-5-methylisoxazoles. Bioorg.Med.Chem.2000,8,2719-2728; (b) Jin-Hua Zhang, Chuan–Dong Fan, Bao-Xiang Zhao. Synthesis and preliminary biological evaluation of novel pyrazo1o[1,5-a]pyrazin-4...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/12C07D405/04
CPCY02P20/584
Inventor 胡向平韩姣
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI