Method for synthesizing alpha, beta-unsaturated amide compound through visible light catalysis

An amide compound, unsaturated technology, applied in the field of visible light catalytic synthesis of α, β-unsaturated amide compounds, to achieve the effect of mild reaction conditions, simple operation, and strong substrate applicability

Active Publication Date: 2020-02-21
MINNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, formamide compounds have the advantages of low price, stable chemical properties, low toxicity and easy operation. They are widely used as reaction solvents in organic synthesis reactions, and formamide compounds are used as precursors of amide groups. So far, few methods have been reported

Method used

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  • Method for synthesizing alpha, beta-unsaturated amide compound through visible light catalysis
  • Method for synthesizing alpha, beta-unsaturated amide compound through visible light catalysis
  • Method for synthesizing alpha, beta-unsaturated amide compound through visible light catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] This example provides a method for the catalytic synthesis of N,N-dimethyl-3,3-diphenylacrylamide by visible light, and the synthesis route is as follows:

[0051]

[0052] The 1,2,3,4-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene is a photocatalyst, and its structural formula is:

[0053]

[0054] Wherein, Cz=carbazol-9-yl.

[0055] Described trifluoroacetic acid-(2,4,6-trimethoxyphenyl) iodine (III) benzene is an oxidizing agent, and its structural formula is:

[0056]

[0057] According to the above synthetic route, the concrete experimental steps are as follows:

[0058] 1) In a nitrogen atmosphere of 1 atmosphere, 1.80 g (10 mmol) of stilbene, 1,2,3,4-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene 0.158g (0.2mmol), trifluoroacetic acid-(2,4,6-trimethoxyphenyl) iodine (III) benzene 9.68g (20mmol), N,N-dimethylformamide 200mL were sequentially added to a dry and clean in a one-mouth bottle;

[0059] 2) Under the temperature condition of 25°C, place the one-mout...

Embodiment 2

[0068] This example provides a method for the catalytic synthesis of 2-(10,11-dihydro-5H-dibenzo[a,d][7]annulene-5-methylene)-N,N-dimethylpropene The method for amide, its synthetic route is as follows:

[0069]

[0070] According to the above synthetic route, the concrete experimental steps are as follows:

[0071] 1) In a nitrogen atmosphere of 1 atmosphere, 2.06 g (10 mmol) of 5-methylene-10,11-dihydro-5H-diphenyl[a,d][7]annulene, 1,2,3 ,4-tetra(carbazol-9-yl)-4,6-dicyanobenzene 0.158g (0.2mmol), trifluoroacetic acid-(2,4,6-trimethoxyphenyl)iodo(III)benzene Add 9.68g (20mmol) and 200mL of N,N-dimethylformamide into a dry and clean single-necked bottle in turn;

[0072] 2) Under the temperature condition of 25°C, place the one-mouth bottle under a blue LED lamp with a light source power of 18W to irradiate the 5-methylene-10,11-dihydro-5H-diphenyl[ a, d][7]annulene disappears (TLC tracking), indicating that the reaction is over, and the reaction solution is obtained at...

Embodiment 3

[0081] This example provides a method for the catalytic synthesis of 3-(4-fluorophenyl)-N,N-dimethyl-3-(2-thienyl)acrylamide under visible light, and the synthesis route is as follows:

[0082]

[0083] According to the above synthetic route, the concrete experimental steps are as follows:

[0084] 1) In a nitrogen atmosphere of 1 atmosphere, 2.04g (10mmol) of 2-[1-(4-fluorophenyl)vinyl]thiophene, 1,2,3,4-tetrakis(carbazol-9-yl) -4,6-dicyanobenzene 0.158g (0.2mmol), trifluoroacetic acid-(2,4,6-trimethoxyphenyl)iodo(III)benzene 9.68g (20mmol), N,N-dimethyl Add 200mL of methyl formamide into a dry and clean single-necked bottle in turn;

[0085] 2) Under the temperature condition of 25°C, place the one-mouth bottle under a blue LED light with a light source power of 18W until the 2-[1-(4-fluorophenyl)vinyl]thiophene disappears (TLC Tracking), indicating that the reaction is over, and the reaction solution is obtained at this time, wherein the one-mouth bottle is 10-15cm awa...

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Abstract

The invention discloses a method for synthesizing an alpha,beta-unsaturated amide compound through visible light catalysis, and belongs to the technical field of organic synthesis. The method comprises the following synthesis steps: subjecting a phenylethylene compound and a formamide compound to a reaction under the conditions of a nitrogen atmosphere and a temperature and under the actions of visible light radiation and synergistic effects of an oxidant and a photocatalyst, and carrying out extracting, drying, concentrating and purifying so as to obtain the alpha,beta-unsaturated amide compound. The method provided by the invention has the advantages of simple and easily-available raw materials, stable chemical properties, mild reaction conditions, simple operation, strong substrate applicability and the like, can be widely applied to drug synthesis and organic molecule synthesis, and has wide industrial application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for catalytically synthesizing α,β-unsaturated amide compounds with visible light. Background technique [0002] α,β-Unsaturated amide compound is a common and valuable organic compound. It not only widely exists in biologically active natural products, but also is often used to construct pharmaceutically active drug molecules, as shown in the following formula : [0003] . [0004] α,β-Unsaturated amides are an important class of organic compounds. The research on it and its derivatives has been carried out for decades at home and abroad. Studies have shown that cinnamic amide derivatives have anticonvulsant, antidepressant, antitumor and cancer cell, as well as the treatment of diabetes and hypertension in clinical application, and are also widely used in pesticides (such as insecticidal and antimutagenic). For example, 2-methylcinnamamide ha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07C233/11C07D295/185C07D333/24C07C235/34C07C233/13C07D317/60
CPCC07C231/12C07D295/185C07D333/24C07D317/60C07C2601/14C07C2603/32C07C233/11C07C235/34C07C233/13Y02B20/00
Inventor 蔡顺有卢茂健黄明强
Owner MINNAN NORMAL UNIV
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