Method for chemically synthesizing diaryl sulfone with asymmetric structure

An asymmetric structure and chemical synthesis technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., to achieve the effects of less environmental pollution, easy availability of raw materials, and cheap raw materials

Active Publication Date: 2018-11-16
QUJING NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to provide a method for chemically synthesizing an asymmetric structure diaryl sulfone; solve the many shortcomings of the existing synthetic asymmetric structure diaryl sulfone, with specific reaction selectivity, mild reaction conditions, Features such as high product yield, high resource utilization rate and low environmental pollution

Method used

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  • Method for chemically synthesizing diaryl sulfone with asymmetric structure
  • Method for chemically synthesizing diaryl sulfone with asymmetric structure
  • Method for chemically synthesizing diaryl sulfone with asymmetric structure

Examples

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example 1

[0029] Example 1. How to set the weight range of raw materials:

[0030] (1) Synthesis of quinoneimine monoketal compounds 3 and 5

[0031]

[0032] Aniline compound 1 (R 1 = H,2-Me,2-OMe,3-F,3-OMe;R 2 = Me,Et, i Pr) as the initial raw material (0.020mol, 2.460 g-4.980 g), after dissolving it in pyridine (20mL), adding p-toluenesulfonyl chloride (TsCl) (0.022 mol, 4.180 g) under ice-cooling conditions, adding After completion, move to room temperature to react for 8-12 hours, and stop the reaction after the reaction of raw material 1 is complete. The pyridine was drained, and the crude product was successively washed with 10% hydrochloric acid, saturated NaHCO 3 The solution was extracted with ethyl acetate 3 times (30mL×3), the organic phase was extracted 3 times with saturated brine (30mL×3), and the organic phase was dried with anhydrous sodium sulfate. The solvent was drained, and the crude product was separated by column chromatography (eluent, petroleum ether: et...

example 2

[0038] Example 2. How to set the raw material weight as a certain value:

[0039] The specific implementation steps are as follows (where 3a and 3b are representative compounds of compound 3, and 5a is a representative compound of compound 5):

[0040] (1) Synthesis of quinoneimine monoketals 3a, 3b and 5a

[0041] (a) Substituted aniline compound 1 (R 1 =H;R 2 =Me) as the initial raw material (0.020 mol, 2.460 g), dissolved it in pyridine (20 mL), added p-toluenesulfonyl chloride (TsCl) (0.022 mol, 4.180 g) under ice-cooling conditions, and moved to React at room temperature for 8 hours, and treat raw material 1 (R 1 =H;R 2 =Me) The reaction was completely stopped. The pyridine was drained, and the crude product was successively washed with 10% hydrochloric acid, saturated NaHCO 3 The solution was extracted with ethyl acetate 3 times (30mL×3), the organic phase was extracted 3 times with saturated brine (30mL×3), the organic phase was separated and dried with anhydrous ...

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PUM

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Abstract

The invention provides a method for chemically synthesizing diaryl sulfone with an asymmetric structure, the method comprises the steps: using substituted aniline compound 1 as an original material, firstly performing Ts (p-toluenesulfonyl) protection or Boc (tert-butoxycarbonyl) protection on aniline to obtain a compound 2 or 4; dissolving compound 2 or 4 in methanol, ethanol or isopropanol at room temperature, performing oxidation on iodobenzene diacetate [PhI(OAc)2] under protection of nitrogen gas to obtain compound 3 or 5; and performing 1,4-conjugate addition reaction / sulfonylation reaction on the compound 5 and compound 6 to obtain diaryl sulfone 7 with an asymmetric structure, under the condition of using triethylenediamine (DABCO) as catalyst and polyethylene glycol (PEG-400) as areaction solvent at 40 DEG C. The invention has the characterized in that raw materials are cheap and easy to obtain, the reaction is specific and selective, the reaction solvent polyethylene glycol(PEG-400) can be recycled for 4 to 5 times, thereby causing small environmental pollution, the yield is high, and popularization and application is convenient and the like.

Description

technical field [0001] The invention belongs to a method for chemically synthesizing an asymmetric structure diaryl sulfone. Background technique [0002] Diaryl sulfones with asymmetric structure are a very important class of sulfur-containing compounds, which have been proved to have many good biological activities, such as high-efficiency antibacterial activity, anti-HIV-1 reverse transcriptase, cyclooxygenase and adenosine tri Phosphatase has a good inhibitory effect. Moreover, diarylsulfone derivatives with asymmetric structure are often used as important reaction intermediates in organic synthesis. [0003] Traditional synthesis methods generally include: (1) oxidation of the corresponding sulfides; (2) transition metal-catalyzed coupling reactions. Recently, four research groups such as Rueping introduced photocatalytic strategies, and successively used transition metal catalysts or transition metal catalysts combined with photocatalysts to catalyze coupling reactio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/42C07C317/34C07C315/00
CPCC07C317/34C07C317/42
Inventor 刘腾成飞翔刘建军夏书标
Owner QUJING NORMAL UNIV
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