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Copper catalytic synthesis method of organic sulphone compound and application

A synthesis method and technology for sulfone compounds, applied in the field of copper-catalyzed synthesis of organic sulfone compounds, can solve the problems of harsh reaction conditions, narrow substrate adaptability, cumbersome reaction steps, etc., and achieve low environmental pollution, easy operation, and functional group compatibility. Good results

Inactive Publication Date: 2018-06-08
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Although these reactions can partially replace SO 2 , but there are still many disadvantages such as harsh reaction conditions, narrow substrate adaptability and cumbersome reaction steps.
Therefore, it remains a formidable challenge to develop a method for organic sulfone synthesis using stable DABSO as a substitute for SO2.

Method used

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  • Copper catalytic synthesis method of organic sulphone compound and application
  • Copper catalytic synthesis method of organic sulphone compound and application
  • Copper catalytic synthesis method of organic sulphone compound and application

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Experimental program
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Effect test

Embodiment 1

[0043]

[0044] At room temperature, charge cuprous oxide (0.02 mmol), 2-phenylimidazo[1,2-a]pyridine (0.2 mmol) into a 25 ml Schlenk tube equipped with a magnetic stirrer , p-methyliodobenzene (0.24 mmol), DABSO (1,4-diazabicyclo[2.2.2]octanebis(sulfur dioxide)) (0.3 mmol), 2 mL of anhydrous DMF was added under nitrogen, and the tube was placed Stir in an oil bath and react at 130°C for 24h. The progress of the reaction was monitored by TLC (Thin Layer Chromatography). After the reaction was completed, the resulting solution was cooled to room temperature, 5 ml of water and 20 ml of ethyl acetate were added to the reaction solution for extraction 4 times, and the organic phase was removed from the solvent by a rotary evaporator. The residue was purified with a silica gel column (silica gel specifications: 200 mesh to 300 mesh, eluent petroleum ether / ethyl acetate (6:1, v / v)) to obtain the target product 2-phenyl-3-toluenesulfonate Acyl imidazo[1,2-a]pyridine 49 mg, yield...

Embodiment 2

[0047]

[0048] At room temperature, charge cuprous oxide (0.02 mmol), 2-phenylimidazo[1,2-a]pyridine (0.2 mmol) into a 25 ml Schlenk tube equipped with a magnetic stirrer , p-chloroiodobenzene (0.24 mmol), DABSO (1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide)) (0.3 mmol), 2 mL of anhydrous DMF was added under nitrogen, and the tube was placed Stir in an oil bath and react at 130°C for 24h. The progress of the reaction was monitored by TLC (Thin Layer Chromatography). After the reaction was completed, the resulting solution was cooled to room temperature, 5 ml of water and 20 ml of ethyl acetate were added to the reaction solution for extraction 4 times, and the organic phase was removed from the solvent by a rotary evaporator. The residue was purified with a silica gel column (silica gel specification: 200 mesh to 300 mesh, eluent petroleum ether / ethyl acetate (5:1, v / v)) to obtain the target product 3-(4-chlorophenylsulfone Acyl)-2-phenylimidazo[1,2-a]pyridine 56 mg,...

Embodiment 3

[0051]

[0052] At room temperature, charge cuprous oxide (0.02 mmol), 2-phenylimidazo[1,2-a]pyridine (0.2 mmol) into a 25 ml Schlenk tube equipped with a magnetic stirrer , p-bromoiodobenzene (0.24 mmol), DABSO (1,4-diazabicyclo[2.2.2]octanebis(sulfur dioxide)) (0.3 mmol), add 2 mL of anhydrous DMF under nitrogen, put the tube into Stir in an oil bath and react at 130°C for 24h. The progress of the reaction was monitored by TLC (Thin Layer Chromatography). After the reaction was completed, the resulting solution was cooled to room temperature, 5 ml of water and 20 ml of ethyl acetate were added to the reaction solution for extraction 4 times, and the organic phase was removed from the solvent by a rotary evaporator. The residue was purified with a silica gel column (silica gel specifications: 200 mesh to 300 mesh, eluent petroleum ether / ethyl acetate (6:1, v / v)) to obtain the target product 3-(4-bromophenylsulfone Acyl)-2-phenylimidazo[1,2-a]pyridine 61 mg, yield 74%.

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Abstract

The invention discloses a copper catalytic synthesis method of an organic sulphone compound and application, and relates to the field of organic synthesis. An imidazol[1,2-a] pyridine compound, a halogenated aromatics compound and DABSO are adopted as raw materials, DMF is adopted as a solvent, monovalent copper is adopted as a catalyst, the reaction temperature is 110 DEG C to 150 DEG C, and a C-3-sulfone-containing imidazol[1,2-a] pyridine compound is high-efficiently synthesized. Compared with a traditional synthesis method, the method has the advantages of mild reaction condition, low cost, little environmental pollution, high yield, good functional group compatibility, convenience in separation and purification and the like.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a copper-catalyzed synthesis method and application of an organic sulfone compound. Background technique [0002] Organic sulfones are a representative type of sulfur-containing compounds that are widely found in bioactive compounds, pharmaceuticals, and agrochemicals. In addition, sulfone groups can also serve as versatile intermediates for chemical transformations in synthetic organic chemistry. Therefore, there is an urgent need to develop an efficient and environmentally friendly method for introducing sulfone groups into organic frameworks in the fields of medicine and synthetic organic chemistry. [0003] Sulfur dioxide (SO 2 ) is often discharged into the air as a large amount of industrial waste gas. Clearly, methods to directly immobilize SO2 in small molecules hold great promise. However, sulfur dioxide gas has disadvantages such as strong corrosiveness and intolera...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07B45/04
CPCC07B45/04C07D471/04
Inventor 杨道山孙鹏飞厉国庆王桦
Owner QUFU NORMAL UNIV
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