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Electrochemical synthesis method of 5-arylthiouracil compound

A technique for the synthesis of arylthiouracil and its synthesis method, which is applied in the field of electrochemical synthesis of 5-arylthiouracil compounds, and can solve the problems of high cost, difficulty in separation and purification, and limitation of industrial application, so as to save raw material cost, The separation and purification of the product is easy, which is conducive to the effect of large-scale production

Active Publication Date: 2020-09-25
HUNAN UNIV OF SCI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method needs to use 2 equivalents of potassium persulfate oxidant and 1.5 equivalents of aromatic thiophenol, not only the separation and purification of the product is difficult and costly, but also produces a large amount of chemical pollutants, which limits the industrial application of this type of method

Method used

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  • Electrochemical synthesis method of 5-arylthiouracil compound
  • Electrochemical synthesis method of 5-arylthiouracil compound
  • Electrochemical synthesis method of 5-arylthiouracil compound

Examples

Experimental program
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Effect test

Embodiment 1～3

[0051] The following examples 1 to 3 are all reacted according to the following reaction equation, mainly to investigate the yield situation of different substrates reacting under optimum conditions:

[0052]

[0053] The specific operation steps are: in a 25mL three-neck round bottom flask, add uracil (0.5mmol), aromatic thiophenol (0.5mmol), tetramethylammonium iodide (0.075mmol), HFIP (8mL), 15mm×15mm The ×3mm RVC electrode is used as the cathode, and the 15mm×15mm×3mm foam nickel electrode is used as the cathode. The resulting mixture was stirred and reacted under a 18mA direct current at room temperature. The progress of the reaction was followed by thin-layer chromatography, and the reaction time was 12 hours. After the reaction, 10ml of water was added and the product was precipitated, filtered and dried to obtain the pure product.

Embodiment 1

[0055]

[0056] Compound A, 5-(phenylthio)pyrimidine-2,4(1H,3H)-dione, 96%

[0057] 1 H NMR (400MHz, DMSO-d6) δ11.41(s, 2H), 7.92(s, 1H), 7.26(t, J=7.8Hz, 2H), 7.15(dd, J=14.2, 7.8Hz, 3H) .

[0058] 13 C NMR (100MHz, DMSO-d6) δ162.9, 151.7, 149.5, 137.3, 129.4, 126.7, 126.0, 102.4.

Embodiment 2

[0060]

[0061] Compound B, 5-(p-tolylthio)pyrimidine-2,4(1H,3H)-dione, 93%

[0062] 1 H NMR (400MHz, DMSO-d6) δ11.36(s, 1H), 11.31(d, J=6.0Hz, 1H), 7.85(d, J=6.0Hz, 1H), 7.14-7.06(m, 4H) ,2.25(s,3H);

[0063] 13 C NMR (DMSO-d6, 100MHz): δ162.2, 151.3, 148.1, 135.2, 132.9, 129.6, 127.2, 103.0, 20.6.

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Abstract

The invention discloses an electrochemical synthesis method of a 5-arylthiouracil compound. The method comprises the following steps: taking a hexafluoroisopropanol solution containing a uracil compound, aromatic thiophenol and iodized salt as an electrolyte, placing an anode and a cathode in the electrolyte, introducing a direct current, and carrying out electrochemical reaction to obtain the 5-arylthiouracil compound. The method has the advantages of mild conditions, simple operation, environment-friendliness, easily available raw materials, excellent compatibility of substrate functional groups, high reaction yield and the like.

Description

technical field [0001] The present invention relates to an electrochemical synthesis method of 5-arylthiouracil compound, in particular to an oxidative dehydrogenation coupling between aromatic thiophenol and uracil catalyzed by iodonium salt under the condition of no external oxidant and under the action of direct current. The invention relates to a method for synthesizing 5-arylthiouracil derivatives through a joint reaction, which belongs to the technical field of organic intermediate synthesis. Background technique [0002] 5-arylthiouracil compounds have a wide range of biological activities and play an important role in the field of drug research and development. Aromatic thiophenol is a very easy-to-obtain raw material. Using aromatic thiophenol as a thioetherification reagent, 5-arylthiourea is prepared through the C-H / C-S oxidative dehydrogenation coupling reaction of uracil and aromatic thiophenol. One of the ideal methods for pyrimidine derivatives. [0003] In ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/02C25B3/10C25B3/23C25B3/29
Inventor 龚绍峰
Owner HUNAN UNIV OF SCI & ENG
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