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Method for constructing 3,5-disubstituted pyridine by utilizing mixed styrene derivative and N,N-dimethylformamide

A technology of styrene derivatives and dimethylformamide, which is applied in the field of synthesis of mixed 3,5-disubstituted pyridine and 3,5-disubstituted pyridine, can solve the problems of low cost of raw materials and catalysts, mild reaction conditions, and the need for Metal catalysis and other problems, to achieve the effects of low cost, mild reaction conditions, and expanded production

Active Publication Date: 2020-08-11
YUANJIANG HUALONG CATALYST TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] In view of the shortcomings of the synthesis method of 3,5-disubstituted pyridine in the prior art, such as high cost of raw materials, need for metal catalysis, and low yield, the purpose of the present invention is to provide a method for mixing styrene derivatives and DMF using iodonium salt catalysis A method for synthesizing 3,5-disubstituted pyridines by one-step oxidative cyclization, the raw materials and catalysts used in the method are low in cost, the reaction conditions are mild, and symmetric and asymmetric 3,5-disubstituted pyridines can be obtained at the same time with high yield

Method used

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  • Method for constructing 3,5-disubstituted pyridine by utilizing mixed styrene derivative and N,N-dimethylformamide
  • Method for constructing 3,5-disubstituted pyridine by utilizing mixed styrene derivative and N,N-dimethylformamide
  • Method for constructing 3,5-disubstituted pyridine by utilizing mixed styrene derivative and N,N-dimethylformamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] The Reaction of 3-Methylstyrene, 2-Chlorostyrene and DMF

[0088]

[0089] The specific operation process of the experiment: add 26mg (0.25mmol) of styrene, 34.5mg (0.25mmol) of 2-chlorostyrene, 405mg (1.5mmol) of potassium peroxodisulfate (K 2 S 2 o 8 ), 124.5 mg (0.75 mmol) of potassium iodide (KI) and 2 mL of N,N-dimethylformamide (DMF). Seal the reaction in an oil bath at 140° C. for 24 hours and take out the sealed tube to stop the reaction. After the temperature dropped to room temperature, 10 mL of sodium chloride (NaCl) aqueous solution and 10 mL of ethyl acetate (EtOAc) were added to the mixture. ) to repeat the extraction 3 times. After removing the residual moisture in the organic phase with anhydrous sodium sulfate, spin dry the organic solvent in the organic phase with a rotary evaporator. The concentrated reaction mixture was separated and purified through a silica gel column to obtain a yellow solid product with a yield of 43%.

[0090] Character...

Embodiment 2

[0092] The Reaction of 3-Methylstyrene, 4-Chlorostyrene and DMF

[0093]

[0094] The specific operation process of the experiment: 26mg (0.25mmol) of styrene, 34.5mg (0.25mmol) of 3-chlorostyrene, 405mg (1.5mmol) of potassium peroxodisulfate (K 2 S 2 o 8 ), 124.5 mg (0.75 mmol) of potassium iodide (KI) and 2 mL of N,N-dimethylformamide (DMF). Seal the reaction in an oil bath at 140° C. for 24 hours and take out the sealed tube to stop the reaction. After the temperature dropped to room temperature, 10 mL of sodium chloride (NaCl) aqueous solution and 10 mL of ethyl acetate (EtOAc) were added to the mixture. ) to repeat the extraction 3 times. After removing the residual moisture in the organic phase with anhydrous sodium sulfate, spin dry the organic solvent in the organic phase with a rotary evaporator. The concentrated reaction mixture was separated and purified through a silica gel column to obtain a yellow solid product with a yield of 49%.

[0095] Characterizat...

Embodiment 3

[0097] Reaction of Styrene, 4-tert-Butylstyrene and DMF

[0098]

[0099] The specific operation process of the experiment: add 26mg (0.25mmol) of styrene, 40mg (0.25mmol) of 4-tert-butylstyrene, 405mg (1.5mmol) of potassium peroxodisulfate (K 2 S 2 o 8 ), 124.5 mg (0.75 mmol) of potassium iodide (KI) and 2 mL of N,N-dimethylformamide (DMF). Seal the reaction in an oil bath at 140° C. for 24 hours and take out the sealed tube to stop the reaction. After the temperature dropped to room temperature, 10 mL of sodium chloride (NaCl) aqueous solution and 10 mL of ethyl acetate (EtOAc) were added to the mixture. ) to repeat the extraction 3 times. After removing the residual moisture in the organic phase with anhydrous sodium sulfate, spin dry the organic solvent in the organic phase with a rotary evaporator. The concentrated reaction mixture was separated and purified through a silica gel column to obtain a yellow solid product with a yield of 56%.

[0100] Characterizatio...

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Abstract

The invention discloses a method for constructing 3,5-disubstituted pyridine by utilizing mixed styrene derivative and N,N-dimethylformamide. The method comprises the following step: subjecting the mixed styrene derivative, N,N-dimethylformamide and peroxydisulfate to a cyclization reaction under the catalytic action of iodized salt so as to obtain symmetrical and asymmetrical mixed 3,5-disubstituted pyridine products at the same time. According to the method, 3,5-disubstituted pyridine is synthesized from the mixed styrene derivative and DMF through one-step oxidative cyclization under the catalysis of iodate; and the method has the advantages of low raw material and catalyst cost, mild reaction conditions, capability of realizing high-yield preparation of the symmetrical and asymmetrical3,5-disubstituted pyridine products at the same time and the like.

Description

technical field [0001] The present invention relates to a synthesis method of 3,5-disubstituted pyridine, in particular to the next step of cyclization using mixed styrene derivatives and N,N-dimethylformamide in peroxodisulfate oxidation and iodine salt catalysis The invention relates to a method for obtaining mixed 3,5-disubstituted pyridines having both symmetrical and asymmetrical structures through reaction, and belongs to the technical field of organic synthesis. Background technique [0002] Pyridine compounds are a class of heterocyclic compounds that have been widely studied so far. Its derivatives are ubiquitous in a variety of natural products and are of great significance in the research of medicine and agricultural chemistry. Among the substituted pyridines, some 3,5-disubstituted pyridines exhibit significant antibacterial activity, such as Sch-21418, that is, 3,5-bis(4-hydroxyphenyl)pyridine has relatively good inhibitory activity on inflammatory factors. In...

Claims

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Application Information

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IPC IPC(8): C07D213/26C07D213/08
CPCC07D213/08C07D213/26
Inventor 郭灿城刘海平郭欣
Owner YUANJIANG HUALONG CATALYST TECH
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