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Synthetic method of aryl sulfone compound containing C (sp2)-S bond

A synthesis method and technology for sulfone compounds, applied in the direction of organic chemistry, etc., can solve the problems of selectivity problem, functional group compatibility, unfavorable industrial application, unfriendly environment, etc., and achieve a simple and efficient preparation method, which is beneficial to industrial application and easy to use in raw materials. the effect

Inactive Publication Date: 2020-07-10
WUYI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, its transition metal catalyst and sulfone source are expensive, and the use of external oxidant is not friendly to the environment, and there are problems such as selectivity and functional group compatibility, which are not conducive to industrial application.

Method used

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  • Synthetic method of aryl sulfone compound containing C (sp2)-S bond
  • Synthetic method of aryl sulfone compound containing C (sp2)-S bond
  • Synthetic method of aryl sulfone compound containing C (sp2)-S bond

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060]

[0061] Add stir bar, DMF (1mL), 1a (59.4mg, 0.2mmol), 2a (106.9mg, 0.6mmol), copper (II) acetate (7.2mg, 0.02mmol), benzoic acid (7.4 mg, 0.03mmol), potassium pivalate (56mg, 0.4mmol), and the reaction system was placed in an oil bath at 80°C for 8h. After the reaction was completed, it was cooled to room temperature, diluted with ethyl acetate (5 mL), washed with water (3 × 20 mL), and then washed with brine (20 mL), the organic phases were combined and washed with anhydrous Na 2 SO 4 After drying and filtration, the filtrate was concentrated and separated by silica gel column chromatography (petroleum ether: ethyl acetate) to obtain a white solid 3a (72.2 mg, 80%, purity greater than 95%). The reaction yield is as high as 80%, and a product with a purity greater than 95% can be obtained by using a simple separation and purification method, indicating that the reaction method has the advantages of high reaction yield and good selectivity.

[0062] Product testin...

Embodiment 2

[0065]

[0066] Add stir bar, DMF (1mL), 1a (72.3mg, 0.2mmol), 2a (106.9mg, 0.6mmol), copper (II) acetate (7.2mg, 0.02mmol), benzoic acid (7.4 mg, 0.03mmol), potassium pivalate (56mg, 0.4mmol), and the reaction system was placed in an oil bath at 80°C for 8h. After the reaction was completed, it was cooled to room temperature, diluted with ethyl acetate (5 mL), washed with water (3 × 20 mL), and then washed with brine (20 mL), the organic phases were combined and washed with anhydrous Na 2 SO 4 After drying and filtering, the filtrate was concentrated and separated by silica gel column chromatography (petroleum ether: ethyl acetate) to obtain a white solid 3b (64.5 mg, 63%, purity greater than 95%).

[0067] Product testing data are as follows: 1 H NMR (400MHz, CDCl 3 )δ10.03(s,1H),8.82(d,J=8.4Hz,1H),8.78(d,J=4.0Hz,1H),8.58(d,J=8.5Hz,1H),8.21(d, J=7.5Hz, 1H), 7.86(d, J=8.1Hz, 2H), 7.68–7.63(m, 3H), 7.56(dd, J=8.5, 4.2Hz, 1H), 7.21(d, J=8.2 Hz, 2H), 2.32(s, 3H). 13 C N...

Embodiment 3

[0069]

[0070] Add stir bar, DMF (1mL), 1a (71.8mg, 0.2mmol), 2a (106.9mg, 0.6mmol), copper (II) acetate (7.2mg, 0.02mmol), benzoic acid (7.4 mg, 0.03mmol), potassium pivalate (56mg, 0.4mmol), and the reaction system was placed in an oil bath at 80°C for 8h. After the reaction was completed, it was cooled to room temperature, diluted with ethyl acetate (5 mL), washed with water (3 × 20 mL), and then washed with brine (20 mL), the organic phases were combined and washed with anhydrous Na 2 SO 4 After drying and filtration, the filtrate was concentrated and separated by silica gel column chromatography (petroleum ether: ethyl acetate) to obtain a white solid 3c (52.41 mg, 51%, purity greater than 95%).

[0071] Product testing data are as follows: 1 H NMR (400MHz, CDCl 3 )δ9.59(s,1H),8.60(d,J=8.1Hz,2H),8.44(d,J=8.5Hz,1H),8.23(d,J=6.7Hz,1H),7.92(d, J=8.1Hz, 2H), 7.63(s, 2H), 7.54(d, J=8.3Hz, 1H), 7.41(d, J=8.1Hz, 3H), 7.25–7.19(m, 2H), 7.16( t, J=7.4Hz, 2H), 7.09(d, J=7....

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Abstract

The invention discloses a synthetic method of an aryl sulfone compound containing a C (sp2)-S bond. The synthetic method comprises the following steps: 1, a 5-chloro-8 aminoquinoline part as shown ina formula (I) is used as a guide group and is prepared from 5-chloro-8 aminoquinoline aromatic amide and aryl sulfinate (II) under the action of a transition metal system. The sulfonylation reaction of the C (sp2)-H bond is achieved through air oxidation, and the compound containing the C (sp2)-S bond shown in the formula (III) is obtained. According to the method, the raw materials are simple andeasy to obtain, operation is easy and convenient, and a concise and efficient synthetic method method is provided for synthesizing aryl sulfonyl compounds.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a C(sp 2 ) The synthetic method of -S bond aryl compound. Background technique [0002] Sulfone group is one of the common structural units in organic molecules, widely present in drug molecules and functional materials, and it also plays an important role in synthetic chemistry, such as the classic Ramberg-Backlund (Ramberg-Backlund) Reaction and Julia olefin synthesis (Julia olefination) reaction. In recent years, the research on the synthesis of sulfone compounds has also become a hot spot. The traditional synthesis methods mainly include the oxidation of sulfides or sulfoxides, the sulfonylation of aromatic hydrocarbons under strong acid conditions, or the addition of sulfonyl radical precursors to alkenes and alkynes. However, these methods usually suffer from the need for multi-step prefunctionalization reactions, poor regioselectivity, or poor functional group compatibi...

Claims

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Application Information

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IPC IPC(8): C07D215/40
CPCC07D215/40
Inventor 梅天胜高君青王向阳张琨李冬利徐学涛
Owner WUYI UNIV
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