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Synthesis method of 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compound

A technology of aniline compounds and synthesis methods, which is applied in the direction of electrolysis process, electrolysis components, electrolysis organic production, etc., can solve the problems of lack of application value, long reaction time, low efficiency, etc., and achieve the green environmental protection of the preparation process and short reaction time Effect

Active Publication Date: 2020-02-28
FUYANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

On the one hand, the addition of photocatalyst is not recyclable; on the other hand, the reaction time is long, the efficiency is low, and the application value is lacking.

Method used

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  • Synthesis method of 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compound
  • Synthesis method of 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compound
  • Synthesis method of 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compound

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preparation example Construction

[0062] A kind of synthetic method of 2-(5-aryl-1,3,4-oxadiazol-2-yl) aniline compound, comprises the steps:

[0063] Electrocatalytic reaction, electrolyte, isatin compound, benzohydrazide compound, solvent, alkali, respectively, are added to the reaction cell, and catalytic electrodes are installed, and the reaction is stirred with electricity;

[0064] Separation and purification, separation and purification of the solution after the electrocatalytic reaction is completed to obtain 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compounds; the 2-(5-aryl- 1,3,4-oxadiazol-2-yl)aniline compounds have the structure shown below:

[0065]

[0066] Among them, R 1 for hydrogen, C 1 ~C 5 Alkyl, C 1 ~C 5 One or more of alkoxy and halogen;

[0067] R 2 is phenyl, substituted phenyl, heterocyclyl, and the substituents in the substituted phenyl are trifluoromethyl, halogen, C 1 ~C 5 Alkyl and C 1 ~C 5 of alkoxy.

[0068] Specifically, in a 10mL non-separated electrolytic cell, the...

Embodiment 1

[0074] Example 1: Put isatin (0.3mmol, 44.1mg), benzohydrazide (0.3mmol, 40.8mg), potassium iodide (0.3mmol, 49.8mg), potassium carbonate (0.3mmol , 41.5mg) and dimethyl sulfoxide (3.0mL), the platinum plate electrode was used as both anode and cathode, and reacted under electric stirring (I=10mA) at 120°C. After the reaction was completed (TLC tracking detection), the residue obtained by spinning was used as the eluent to pass the chromatographic column to obtain the product 2-(5-phenyl-1,3,4-oxadiazole- 2-yl) aniline compound with a yield of 77%.

[0075] The 2-(5-phenyl-1,3,4-oxadiazol-2-yl) aniline product is analyzed by nuclear magnetic resonance spectrometer, the results can be found in Figure 1~2 , figure 1 For the 2-(5-phenyl-1,3,4-oxadiazol-2-yl) aniline product that the embodiment of the present invention 1 provides 1 H NMR ( 1 H-NMR) spectrogram; figure 2 For the 2-(5-phenyl-1,3,4-oxadiazol-2-yl)aniline product provided in Example 1 of the present invention ...

Embodiment 2

[0079] Example 2: Put isatin (0.3mmol, 44.1mg), 4-methylbenzohydrazide (0.3mmol, 45.1mg), potassium iodide (0.3mmol, 49.8mg), carbonic acid in a 10mL electrolytic cell without separation Potassium (0.3 mmol, 41.5 mg) and dimethyl sulfoxide (3.0 mL) were reacted at 120° C. under electric stirring (I=10 mA), and the platinum plate electrode was used as both the anode and the cathode. After the reaction was completed (TLC tracking detection), the residue obtained by spinning was used as an eluent to pass the chromatographic column to obtain the product 2-(5-(p-methylphenyl)-1,3, 4-oxadiazol-2-yl)aniline compound, the yield was 83%.

[0080] The 2-(5-(p-methylphenyl)-1,3,4-oxadiazol-2-yl) aniline product is analyzed by nuclear magnetic resonance spectrometer, the results can be found in Figure 3-4 , image 3 For the 2-(5-(p-methylphenyl)-1,3,4-oxadiazol-2-yl)aniline product that the embodiment of the present invention 2 provides 1 H NMR ( 1 H-NMR) spectrogram; Figure 4 For...

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Abstract

The invention discloses a synthesis method of a 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compound. The method comprises the following steps: respectively adding an electrolyte, substituted isatin, substituted benzoyl hydrazine, a solvent, an alkali and an electrode into a non-separated electrolytic cell, and carrying out electrifying and stirring for a reaction; and subjecting a solution obtained after the reaction to separating and purifying so as to obtain the 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compound. According to the method, no metal or chemical oxidant is needed in the preparation process; reaction time is short; and the preparation process is green and environmentally friendly.

Description

technical field [0001] The invention relates to the technical field of synthesis of aniline compounds, in particular to a synthesis method of 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compounds. Background technique [0002] 2,5-Diaryl-1,3,4-oxadiazoles are an important class of oxygen-containing heterocycles, which widely exist in bioactive molecules and optoelectronic materials. In particular, 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compounds, due to the presence of amino groups in their molecules, provide the possibility for further conversion into useful organic molecules. Therefore, its synthesis has always been the research focus of organic chemists. However, due to the compatibility of amino groups in the system, there are few reports on 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compounds. [0003] In 2015, Wu's group synthesized 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compounds (C . Xu, F-C. Jia, Q. Cai, D-K. Li, Z-W. Zhou and A-X. Wu, Chem. Commun, 2015, 51, 6629.). Alt...

Claims

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Application Information

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IPC IPC(8): C25B3/00
CPCC25B3/00
Inventor 钱朋沈毅银
Owner FUYANG NORMAL UNIVERSITY
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