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A kind of preparation method of asymmetric organic persulfur compound

A compound, asymmetric technology, applied in the preparation of hydrogenated polysulfides/polysulfides, organic chemistry, preparation of sugar derivatives, etc. And other issues

Active Publication Date: 2021-07-20
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this strategy, the preparation of persulfide reagents is extremely cumbersome
[0010] In addition, the Chinese invention patent application with the publication number CN104387303A discloses a redox mechanism using sulfur, using sodium sulfinic acid with halogenated hydrocarbons and Na 2 S 2 o 3 As the reaction raw material, under the action of no transition metal, the method of obtaining aryl-aryl, aryl-alkyl, alkyl-alkyl asymmetric persulfide compounds by reaction, the method system is complex, raw materials sodium thiosulfate and The material ratio of halogenated hydrocarbons and sodium sulfinic acid is high, and the one-pot reaction cannot be realized, and the operation is cumbersome, and the reaction solvent is a mixture of organic solvent and water, so it is impossible to realize the oversulfurization modification of sugar groups
[0011] There are many deficiencies in the above methods: the reagents used in the reaction are highly toxic or corrosive, the raw materials are not easy to obtain, the reaction process is demanding, the production cost is high, and the environment is polluted.

Method used

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  • A kind of preparation method of asymmetric organic persulfur compound
  • A kind of preparation method of asymmetric organic persulfur compound
  • A kind of preparation method of asymmetric organic persulfur compound

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Experimental program
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Effect test

reference example 1

[0067] Reference example 1 synthetic intermediate formula (II-1) compound

[0068]

[0069] Among them, R 2 , m, ring A is as defined in the present invention.

[0070] Add 4 mL of toluene to a 10 mL two-neck Schlenk tube. in N 2 Under atmosphere, add formula (IV-1) compound (0.5mmol), CuI (10mol%, 0.05mmol), 1,10-phenanthroline (20mol%, 0.1mmol), finally add potassium thioacetate (1.5 equivalent, 0.75mmol), the reaction mixture was reacted at 100°C for 24h. Cool at room temperature, pour into diethyl ether (20 mL) and water (20 mL), separate the organic phase, and extract the aqueous phase with 2 equal parts of diethyl ether (20 mL), combine the organic phases, wash with anhydrous Na 2 SO 4 After drying and filtering, the crude product is separated by column chromatography to obtain the compound of formula (II-1).

reference example 2

[0071] Reference example 2 synthetic intermediate formula (II-2) compound

[0072]

[0073] Among them, R 2 , m, ring A is as defined in the present invention; X is Cl or Br.

[0074] Dissolve the compound of formula (IV-2) (1 equivalent) in DMF, add potassium thioacetate (1.5 equivalents) and stir at 70°C, monitor the reaction by TLC until RX disappears, add brine and ethyl acetate, separate The organic layer was extracted with ethyl acetate, and the combined organic layers were washed with brine and washed with Na 2 SO 4 Drying and evaporation in vacuo afforded the crude compound of formula (II-2), which was used in the next step without purification.

reference example 3

[0075] Reference example 3 synthetic intermediate formula (II-3) compound

[0076]

[0077] Dissolve the compound of formula (IV-3) (1 equivalent) in DMF, add potassium thioacetate (1.5 equivalents) and stir at room temperature, add brine and ethyl acetate, separate the organic layer, and extract the aqueous phase with ethyl acetate , the combined organic layers were washed with brine, washed with Na 2 SO 4 Drying and evaporation in vacuo afforded crude compound of formula (II-3). The crude product was used in the next step without purification.

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Abstract

The invention discloses a method for preparing an asymmetric organic persulfur compound, comprising the following steps: under the catalysis of a base, a compound of formula (II), compound of formula (III) and sodium thiosulfate are reacted in a solvent in one pot, The asymmetric organic persulfur compound represented by formula (I) is obtained. The preparation method of the invention has mild reaction conditions, simple operation and high yield; and can realize the oversulfurization modification of quinolinone, coumarin, glucose and other natural product molecules.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of an asymmetric organic persulfur compound. Background technique [0002] Asymmetric organic persulfide compounds are a class of compounds containing persulfide bonds (S-S). They are named for the different groups at both ends of the persulfide bonds. They are a class of sulfur-containing organic compounds with great application prospects. [0003] In the field of natural products, polythiodiketopiperazines and their derivatives (ETPs) are outstanding representatives of asymmetric organic persulfur compounds. More than 126 kinds of ETPs have been discovered so far, and their good anti-inflammatory and antibacterial effects have been confirmed. [0004] In clinical medicine, asymmetric organic persulfide compounds have been used as drugs. Such as prothiolamine and furathiamine for the treatment of vitamin B1 deficiency; romidepsin for the treatme...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/24C07C323/20C07C323/56C07C323/62C07C321/28C07C323/16C07C323/07C07C321/20C07D307/10C07H13/04C07H1/00C07D311/16
CPCC07C319/24C07D307/10C07D311/16C07H1/00C07H13/04C07C323/20C07C323/56C07C323/62C07C321/28C07C323/16C07C323/07C07C321/20
Inventor 潘远江王敦盖高展
Owner ZHEJIANG UNIV
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