Green synthesis method of imidazoline under visible light catalysis

A green synthesis technology of imidazoline, applied in the direction of organic chemistry, can solve the problems of low efficiency, difficult to obtain raw materials, many synthesis steps, etc., and achieve the effect of easy to obtain raw materials, cheap raw materials, and green and mild reaction conditions

Active Publication Date: 2020-06-16
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The above methods have the disadvantages that the raw materials are not easy to obtain, the synthesis steps are relatively many, and the efficiency is low; in addition, the catalyst dosage, reaction selectivity control, substrate expansion, etc. need to be further studied. Therefore, it is necessary to develop a green and efficient, The synthesis method of imidazoline with mild conditions, environmental friendliness, simple and easy-to-obtain raw materials and high selectivity is of great significance

Method used

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  • Green synthesis method of imidazoline under visible light catalysis
  • Green synthesis method of imidazoline under visible light catalysis
  • Green synthesis method of imidazoline under visible light catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] In a dry 10mL Schlenk tube, add 90.4mg N-phenylglycine, 24.7mg p-methoxyaniline, 2.6mg photocatalyst {Ir[dF(CF 3 )ppy] 2 bpy}PF 6 , 12.1mg oxidant Co(dmgH 2 ) 2 PyCl, 2 mL of 1,2-dichloroethane, 21.2 mg of benzaldehyde, the ratio of benzaldehyde: p-methoxyaniline: N-phenylglycine: photocatalyst: oxidant is 1:1:3:0.01:0.15. The reaction bottle was pumped and ventilated three times to ensure that the reaction tube was anhydrous and oxygen-free, then sealed, and the reaction was placed under 455nm blue light (Blue LED light) and stirred for 2 hours. The distance between the Blue LED light and the Schlenk tube was 3cm. After the TLC detection reaction was completed, the reaction solution was transferred to an eggplant-shaped bottle, an appropriate amount of silica gel was added to concentrate under reduced pressure, and the resulting residue was purified by column chromatography (PE / EA=100:1), as Figure 1-2 As shown, the synthesized product was 3-(4-methoxyphenyl)-1,4-...

Embodiment 2

[0069] In a dry 10mL Schlenk tube, add 90.4mg N-phenylglycine, 24.7mg p-methoxyaniline, 2.6mg photocatalyst {Ir[dF(CF 3 )ppy] 2 bpy}PF 6 , 12.1mg oxidant Co(dmgH 2 ) 2 PyCl, 2mL1,2-dichloroethane, 24.1mg p-tolualdehyde, p-tolualdehyde: p-methoxyaniline: N-phenylglycine: photocatalyst: the ratio of the substance quantity of oxidizing agent is 1:1: 3:0.01:0.15. The reaction bottle was pumped and ventilated three times to ensure that the reaction tube was anhydrous and oxygen-free, then sealed, and the reaction was placed under 455nm blue light (Blue LED light) and stirred for 2 hours. The distance between the Blue LED light and the Schlenk tube was 3cm. After the TLC detection reaction was completed, the reaction solution was transferred to an eggplant-shaped bottle, an appropriate amount of silica gel was added to concentrate under reduced pressure, and the resulting residue was purified by column chromatography (PE / EA=100:1), as Figure 3-4 As shown, the synthesized produ...

Embodiment 3

[0071] In a dry 10mL Schlenk tube, add 90.4mg N-phenylglycine, 24.7mg p-methoxyaniline, 2.6mg photocatalyst {Ir[dF(CF 3 )ppy] 2 bpy}PF6 , 12.1mg oxidant Co(dmgH 2 ) 2 PyCl, 2mL1,2-dichloroethane, 24.9mg o-fluorobenzaldehyde, o-fluorobenzaldehyde: p-methoxyaniline: N-phenylglycine: photocatalyst: oxidizing agent The amount of substance is 1:1:3: 0.01:0.15. The reaction bottle was pumped and ventilated three times to ensure that the reaction tube was anhydrous and oxygen-free, then sealed, and the reaction was placed under 455nm blue light (Blue LED light) and stirred for 2 hours. The distance between the Blue LED light and the Schlenk tube was 3cm. After the TLC detection reaction was completed, the reaction solution was transferred to an eggplant-shaped bottle, an appropriate amount of silica gel was added to concentrate under reduced pressure, and the resulting residue was purified by column chromatography (PE / EA=100:1), as Figure 5-6 As shown, the synthesized product is...

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PUM

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Abstract

The invention discloses a green synthesis method of imidazoline under visible light catalysis, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: 1) adding N-phenylglycine, a photocatalyst, an oxidant, a solvent, an arylamine compound, an aldehyde compound or an imine compound into a dry Schlenk tube; 2) carrying out air suction and exchange operations on the reaction bottle filled with the material for three times so as to ensure that no water or oxygen exists in the reaction tube and then sealing the reaction tube; 3) placing the reaction bottle under the irradiation of a Blue LED, carrying out a stirring reaction, and ending the reaction when TLC detects that the aldehyde compound disappears; and 4) transferring the reaction solution in the Schlenk tube into an eggplant-shaped bottle, adding a proper amount of silica gel, concentrating under reduced pressure, and purifying the obtained residue by column chromatography to obtain the product imidazoline. Compared with the prior art, the method has the characteristics of simple synthetic route, cheap and easily available raw materials without synthesis, simplicity and convenience in operation, environmental friendliness, mild reaction conditions, wide substrate application range and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a green synthesis method of imidazoline under visible light catalysis. Background technique [0002] Imidazoline, the chemical formula is: It is a very important N-containing heterocyclic compound. There is one N atom at the 1 and 3 positions of the ring respectively, and the presence of two N atoms makes imidazoline somewhat basic. In addition, the lone pair of electrons on the N atom can coordinate with metal ions to obtain coordination compounds with variable structures. Imidazoline compounds are widely used in the fields of chemistry, biology, and medicine, such as (-)-Dysibetaine PP, Chaetominine, Kifunensine, etc. In addition, in the field of pesticides, imidazoline compounds also play an important role. For example, iprodione, as a high-efficiency spectrum, contact fungicide, can inhibit the germination and production of fungal spores, as well as ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/02C07D417/04C07D409/04
CPCC07D233/02C07D417/04C07D409/04Y02P20/584
Inventor 曾晓飞钟国富潘舒蕾
Owner HANGZHOU NORMAL UNIVERSITY
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