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Method for preparing dithiocoumarin benzothiophene compound through platinum catalysis

A technology of dithiocoumarin and benzothiophene, applied in the direction of organic chemistry, etc., can solve the problems of low reaction efficiency and many reaction steps, etc.

Inactive Publication Date: 2020-11-20
JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The reported preparation method of dithiocoumarinabenzothiophene compounds is mainly through metal catalysis, and can be prepared after multi-step substitution and esterification, which has the disadvantages of many reaction steps and low reaction efficiency.

Method used

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  • Method for preparing dithiocoumarin benzothiophene compound through platinum catalysis
  • Method for preparing dithiocoumarin benzothiophene compound through platinum catalysis
  • Method for preparing dithiocoumarin benzothiophene compound through platinum catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The product of Preparation 4a: Example 1

[0041] At room temperature in a round bottom flask was added 25mL of so 5mmol2- mercapto cinnamic acid, 6mmol carbon disulfide, and 2-bromothiophenol 5mmol then successively added 15mL acetonitrile, 0.5mmol platinum chloride and 10mmol sodium in ethanol, the reaction was stirred at 80 ℃ 8 hours. After cooling, to the system was added 20mL saturated sodium chloride aqueous solution, and extracted 3 times with ethyl acetate, 20mL each, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was evaporated, 200-300 mesh silica gel column chromatography to give coumarin and the dithiophosphoric benzothiophene compound 4a (1278mg, 90% yield, yellow powder). 4a 1 H NMR spectra, see figure 1 , 13 C NMR spectra see figure 2 .

[0042] 5,11-Dithia-benzo [a] fluorene-6-thione (4a)

[0043] 1 H NMR (500MHz, CDCL 3 ): Δ8.15 (dd, J 1 = 2.4Hz, J 2 = 6.6Hz, 1H), 8.05 (dd, J 1 = 1.5Hz, J 2 = 7.8Hz, 1H), 7.68 (dd, J 1 = 1...

Embodiment 2

[0046] 4b Preparation of the product: Example 2

[0047] At room temperature, so a round bottom flask was added 25mL of 5mmol2- mercapto cinnamic acid, 6mmol 5mmol carbon disulfide and 2-bromo-5-methyl thiophenol in acetonitrile followed by addition of 15mL, 0.5mmol platinum chloride and 10mmol of sodium in ethanol, and the reaction was stirred at 80 ℃ 8 hours. After cooling, to the system was added 20mL saturated sodium chloride aqueous solution, and extracted 3 times with ethyl acetate, 20mL each, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was evaporated, 200-300 mesh silica gel column chromatography to give coumarin and the dithiophosphoric benzothiophene compound 4b (1356mg, 91% yield, yellow powder). 4b 1 H NMR spectra, see image 3 , 13 C NMR spectra see Figure 4 .

[0048] 9-Methyl-5,11-dithia-benzo [a] fluorene-6-thione (4b)

[0049] 1 H NMR (500MHz, CDCL 3 ): Δ7.98 (m, 3H), 7.91 (s, 1H), 7.55-7.61 (m, 2H), 7.52 (d, J = 8.5Hz, 1H), 7.49...

Embodiment 3

[0051] 4c Preparation of the product: Example 3

[0052] At room temperature, so a round bottom flask was added 25mL of 5mmol2- mercapto cinnamic acid, 6mmol 5mmol carbon disulfide and 2-bromo-4-methyl thiophenol in acetonitrile followed by addition of 15mL, 0.5mmol platinum chloride and 10mmol of sodium in ethanol, and the reaction was stirred at 80 ℃ 8 hours. After cooling, to the system was added 20mL saturated sodium chloride aqueous solution, and extracted 3 times with ethyl acetate, 20mL each, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was evaporated, 200-300 mesh silica gel column chromatography to give coumarin and the dithiophosphoric benzothiophene compound 4c (1222mg, 82% yield, yellow powder). 4c 1 H NMR spectra, see Figure 5 , 13 C NMR spectra see Image 6 .

[0053] 8-Methyl-5,11-dithia-benzo [a] fluorene-6-thione (4c)

[0054] 1 H NMR (500MHz, CDCL 3 ): Δ7.98 (m, 3H), 7.91 (s, 1H), 7.55-7.61 (m, 2H), 7.52 (d, J = 8.5Hz, 1H), 7....

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Abstract

The invention discloses a method for preparing a dithiocoumarin benzothiophene compound shown as a formula (IV) through platinum catalysis. The preparation method comprises the following steps: preparing a reaction product from a 2-mercaptocinnamic acid compound as shown in a formula (I), carbon disulfide as shown in a formula (II) and a 2-bromophenol compound as shown in a formula (III) by takingplatinum chloride as a catalyst, sodium ethoxide as alkali and acetonitrile as a medium, and carrying out aftertreatment on the reaction product to obtain the dithiocoumarin benzothiophene compound.The method has the advantages of wide raw material source, simple operation, simple treatment after reaction, excellent yield and the like. The method has an important application prospect in the industrial field of synthesis of related medical intermediates.

Description

Technical field [0001] The present invention belongs to the technical field for preparing a pharmaceutical intermediate, particularly relates to the preparation of a platinum catalyzed dithio-benzo thiophene and coumarin compounds. Background technique [0002] Sulfur-containing heterocyclic pharmaceutical industry within a class of important organic synthesis intermediates. In the present sulfur-containing heterocyclic compounds, and efficient preparation of benzothiophene derivatives is one of the hotspots. Benzothiophene and derivatives having therapeutic potential in many natural and synthetic molecules structurally similar, facilitate the generation of new drug development in the molecular structure. Benzothiophene skeleton structure advantage in drug development, it has a variety of biological activities, such as anticancer, anti-inflammatory, anti-oxidation, anti-tuberculosis, anti-diabetic, anti-convulsant effect and the like. In addition, many coumarin and the dithiophos...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 许睿雯徐润生李雪琴
Owner JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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