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A kind of preparation method of alkali-promoted asymmetric organic persulfur compound

A compound and asymmetric technology, applied in organic chemistry, thioether preparation, steroids, etc., can solve the problems of complex system, harsh reaction process requirements, high production cost, etc., achieve cheap and easy raw materials, reduce feeding costs, avoid The effect of using

Active Publication Date: 2021-11-19
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method system is complicated, and the material ratio of the raw material sodium thiosulfate, halogenated hydrocarbon and sodium sulfinic acid is high, and the one-pot reaction cannot be realized
[0008] 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 alkali-promoted asymmetric organic persulfur compound
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  • A kind of preparation method of alkali-promoted asymmetric organic persulfur compound

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reference example 1

[0067] Synthesis of reference example 1 raw material formula (II) compound

[0068]

[0069] Among them, R 2 , Ring A is as defined in the present invention; Y is Cl or Br.

[0070] Add 4 mL of acetonitrile to a 10 mL two-neck Schlenk tube. Compound of formula (IV-1) (0.5 mmol) and compound of formula (V) (1.5 equivalents, 0.75 mmol) were added, and the reaction mixture was reacted at 100°C for 3 h, then turned to room temperature, and stirred overnight. Filtrate and concentrate the filtrate to obtain a crude product, which is separated by column chromatography to obtain a compound of formula (II).

reference example 2

[0071] Reference example 2 synthesis of raw material formula (II) compound

[0072]

[0073] Among them, R 2 , Ring A is as defined in the present invention.

[0074] Dissolve the compound of formula (IV-2) (1 equivalent) in acetonitrile, add the compound of formula (V) (1.5 equivalents), NBS (2.0 equivalents) and stir at room temperature, monitor the reaction by TLC, until the raw material disappears, add brine and ethyl acetate, the organic layer was separated, the aqueous phase was extracted with ethyl acetate, the combined organic layer was washed with brine, and washed with Na 2 SO 4 Drying and evaporation in vacuo afforded a crude product of the compound of formula (II-2), which was separated by column chromatography to give the compound of formula (II).

Embodiment 1

[0076]

[0077] In a dry 25 mL Schlenk reaction tube, add 0.5 mmol of 4-methoxyphenyl thiosulfonate, 1.0 mmol of thiourea, 1.0 mmol of benzyl bromide, 0.5 mmol of potassium carbonate, and 3 mL of toluene. Stir at 80°C for 24 hours. After the reaction, cool to room temperature, filter, concentrate the filtrate, and directly pass through a silica gel column (the volume ratio of ethyl acetate to petroleum ether is 1:50-1:3) to obtain the product with a yield of 92%.

[0078] 1 H NMR (400MHz, CDCl 3 )δ7.36–7.27(m,5H),7.18–7.15(m,2H),6.87–6.85(m,2H),3.81(s,3H),3.65(s,2H),3.57(s,2H) ; 13 C NMR (100MHz, CDCl 3 ) δ 159.0, 137.4, 130.5, 129.4, 129.2, 128.4, 127.4, 113.8, 55.2, 43.3, 42.7.

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Abstract

The invention discloses a preparation method of an asymmetric organic persulfur compound, which comprises the following steps: under the promotion of a base, the compound of formula (I), the compound of formula (II) and thiourea are reacted in one pot to obtain the compound of formula (III) The asymmetric organic persulfide compounds shown. The preparation method of the invention has mild reaction conditions, simple operation and high yield. It can prepare organic persulfur compounds and realize the persulfurization modification of drug molecules such as acetaminophen and estrone, as well as natural product molecules such as zingerone and amino acids.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of an asymmetric organic persulfur compound. Background technique [0002] Asymmetric organic persulfur compounds are a class of sulfur-containing organic compounds with extremely high medical value. Currently commercially available sulfur-containing drugs, such as prothiolamine, furathiamine, and romidepsin, all have sulfur bridges . In natural product chemistry, more than 120 polythiodiketopiperazines and their derivatives have been discovered, and their good anti-inflammatory and antibacterial effects have also attracted the attention of medicinal chemists. At the same time, in the research of targeted drugs, this compound with disulfide bonds is a good carrier for drug delivery and release. For this reason, chemists have intensified their efforts in the development of asymmetric organic persulfur compounds in recent years. [0003] At present, the meth...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/14C07C323/16C07C323/56C07C323/65C07C323/09C07C323/20C07C323/42C07C323/12C07D333/34C07D209/48C07C323/52C07D215/227C07D215/12C07D311/18C07D309/04C07J31/00C07D307/79C07D211/24C07C323/59
CPCC07C319/14C07D209/48C07D211/24C07D215/12C07D215/227C07D307/79C07D309/04C07D311/18C07D333/34C07J31/006C07C2602/08C07C323/16C07C323/56C07C323/65C07C323/09C07C323/20C07C323/42C07C323/12C07C323/52C07C323/59
Inventor 潘远江王敦盖
Owner ZHEJIANG UNIV
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