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Method for preparing beta-ketosulfone compound through visible light mediated atopic acid decarboxylation ketonization reaction

A technology for decarboxylation ketones and compounds of atropic acid, which is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry and other directions, can solve problems such as excess, complicated deoxygenation operations, heavy metal residues, etc., and achieves mild reaction conditions and simple raw materials. Easy to obtain, no metal residue effect

Active Publication Date: 2020-04-10
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, from the perspective of environmental protection and practical operation, these published synthetic routes still have some deficiencies: complex oxygen removal operations, harmful free radical initiators, unavailable starting materials, excessive inorganic salt additives, Heavy metal residues, etc.

Method used

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  • Method for preparing beta-ketosulfone compound through visible light mediated atopic acid decarboxylation ketonization reaction
  • Method for preparing beta-ketosulfone compound through visible light mediated atopic acid decarboxylation ketonization reaction
  • Method for preparing beta-ketosulfone compound through visible light mediated atopic acid decarboxylation ketonization reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Preparation of compound 3aa (1-phenyl-2-(phenylsulfonyl)ethan-1-one), the preparation method is as follows:

[0052] (1) According to the molar ratio of 1:1.5:0.03:1:1, add atropic acid 1 (compound with structural formula 1-1), sulfonyl hydrazide 2 (compound with structural formula 2-1), fluorescein, alkali (NaHCO 3 ) and KI, fully dissolved in the mixed solvent of acetonitrile and water (the volume ratio of acetonitrile and water is 5.5:1), connected to the oxygen balloon under sealed conditions, and reacted under the illumination conditions of a compact fluorescent light of 23W, and the reaction process was performed by TLC Monitoring, detecting that the reaction of atropic acid 1 in the system is completed and the reaction can be ended;

[0053] (2) Concentrate the reaction mixture after the reaction under reduced pressure, add water to the concentrate, extract with ethyl acetate, combine the organic layers, wash with saturated brine and wash with anhydrous Na 2 SO...

Embodiment 2

[0057] Preparation of compound 3ab (1-phenyl-2-tosylethan-1-one), the preparation method is as follows:

[0058] (1) According to the molar ratio of 1:1.5:0.03:1:1, add atropic acid 1 (compound with structural formula 1-1), sulfonyl hydrazide 2 (compound with structural formula 2-2), fluorescein, alkali (NaHCO 3 ) and KI, fully dissolved in the mixed solvent of acetonitrile and water (the volume ratio of acetonitrile and water is 5.5:1), connected to the oxygen balloon under sealed conditions, and reacted under the illumination conditions of a compact fluorescent light of 23W, and the reaction process was performed by TLC Monitoring, detecting that the reaction of atropic acid 1 in the system is completed and the reaction can be ended;

[0059] (2) Remove acetonitrile by rotary evaporation after the reaction, add water to the obtained concentrated reaction mixture, extract with ethyl acetate, combine the organic phases, wash with saturated brine and wash with anhydrous Na 2 ...

Embodiment 3

[0063] Preparation of compound 3ac (2-((4-methoxyphenyl)sulfonyl)-1-phenylethan-1-one), the preparation method is as follows:

[0064] (1) According to the molar ratio of 1:1.5:0.03:1:1, add atropic acid 1 (compound with structural formula 1-1), sulfonyl hydrazide 2 (compound with structural formula 2-3), fluorescein, alkali (NaHCO 3 ) and KI, fully dissolved in the mixed solvent of acetonitrile and water (the volume ratio of acetonitrile and water is 5.5:1), connected to the oxygen balloon under sealed conditions, and reacted under the illumination conditions of a compact fluorescent light of 23W, and the reaction process was performed by TLC Monitoring, detecting that the reaction of atropic acid 1 in the system is completed and the reaction can be ended;

[0065] (2) After the reaction was completed, acetonitrile was removed by rotary evaporation, water was added to the obtained concentrated reaction mixture, extracted with ethyl acetate, the organic layers were combined, ...

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Abstract

The invention relates to a method for preparing a beta-ketosulfone compound through a visible light mediated atopic acid decarboxylation ketonization reaction, and belongs to the field of compound preparation. According to the method disclosed by the invention, environment-friendly atortic acid with wide sources and stable odorless sulfonyl hydrazine are used as reactants, fluorescein, inorganic base and potassium iodide are added and then fully dissolved in a mixed solvent of acetonitrile and water, a reaction is carried out in an oxygen atmosphere (communicated with oxygen spheres), and thebeta-ketosulfone compound can be obtained through the reaction under visible light irradiation. The preparation method disclosed by the invention has the characteristics of simple and easily availableraw materials, simple operation, mild reaction conditions, no metal residue and insensitivity of a reaction system to water.

Description

technical field [0001] The invention belongs to the field of compound preparation, and in particular relates to a method for preparing β-ketosulfone compounds through a visible light-mediated decarboxylation reaction of atropic acid. Background technique [0002] Decarboxylation reaction has attracted much attention in contemporary synthetic methodology due to its many advantages such as wide source of raw materials, low synthesis cost, high conversion rate of raw materials, and few by-products. In this type of conversion, the starting material often reacts under the activation of the carboxyl group, and the carboxyl group is removed in the subsequent reaction process to obtain the target product that is not easy to achieve by other methods, which also reflects the importance of this reaction in organic methodology. Advantage. So far, in addition to the traditional metal-catalyzed decarboxylation methods, light-mediated decarboxylation reactions have also shown promising de...

Claims

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Application Information

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IPC IPC(8): C07B45/04C07C315/00C07C317/24C07C317/44C07D333/34
CPCC07B45/04C07C315/00C07D333/34C07C317/24C07C317/44Y02P20/584
Inventor 官智何延红陈洁
Owner SOUTHWEST UNIVERSITY
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