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A method for synthesizing alkyne sulfone compounds from terminal alkynes and sulfonyl hydrazides under electrochemical conditions

A synthesis method and terminal alkyne technology, applied in electrolysis components, drug combination, electrolysis process, etc., to achieve mild reaction conditions, high atom economy, and simple synthesis steps

Active Publication Date: 2021-07-02
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods generally require the use of alkyne halides or alkyne acids as substrates, and the use of excess oxidants and metal catalysts. Therefore, direct use of terminal alkynes without the use of metal catalysts and oxidants can efficiently and environmentally friendly construct alkyne sulfur bonds to synthesize alkyne sulfone compounds. It is a very meaningful work, but there is still no literature report

Method used

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  • A method for synthesizing alkyne sulfone compounds from terminal alkynes and sulfonyl hydrazides under electrochemical conditions
  • A method for synthesizing alkyne sulfone compounds from terminal alkynes and sulfonyl hydrazides under electrochemical conditions
  • A method for synthesizing alkyne sulfone compounds from terminal alkynes and sulfonyl hydrazides under electrochemical conditions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Preparation and characterization of 1-methoxy-4-(tosylethynyl)benzene (3aa):

[0018]

[0019] Add 0.25mmol of p-methoxyphenylacetylene, 1mmol of p-toluenesulfonyl hydrazide, 2 equivalents of potassium iodide and 2 equivalents of cesium carbonate to a 25mL three-neck flask, add 18mL of acetonitrile and water mixed solution to dissolve, and use reticulated glassy carbon RVC was used as the anode and the platinum sheet was used as the cathode. The stirring reaction was carried out at 1.0V constant voltage, oxygen atmosphere, and 50°C for 2 hours. TLC monitored the reaction process. After the reaction was completed, the mixture was extracted with 10 mL ethyl acetate, and the organic layer was used Anhydrous MgSO 4 Drying, the solvent was spin-dried under reduced pressure, and passed through column chromatography (SiO 2 , ethyl acetate / petroleum ether=1:12) to purify the residue to obtain 3aa as pale yellow solid.

[0020] The product is characterized by:

[0021] Pal...

Embodiment 2

[0023] Preparation and characterization of 1-methoxy-4-((benzenesulfonyl)ethynyl)benzene (3ab):

[0024]

[0025] Add 0.25mmol of p-methoxyphenylacetylene, 1mmol of benzenesulfonyl hydrazide, 2 equivalents of ammonium iodide and 2 equivalents of potassium carbonate to a 25mL three-necked flask, add 18mL of acetonitrile and water mixed solution to dissolve, and use a reticulated glass Carbon RVC was used as the anode, and the platinum sheet was used as the cathode. Stirring reaction was carried out at 1.2V constant voltage, oxygen atmosphere, and 40°C for 3 hours. TLC monitored the reaction progress. After the reaction was completed, the mixture was extracted with 10mL ethyl acetate, and the organic layer was with anhydrous MgSO 4 Drying, the solvent was spin-dried under reduced pressure, and passed through column chromatography (SiO 2 , ethyl acetate / petroleum ether=1:10) to obtain 3ab as a yellow oily liquid.

[0026] The product is characterized by:

[0027] Yellow oil...

Embodiment 3

[0029] Preparation and characterization of 1-(((4-methoxyphenyl)ethynyl)sulfonyl)-2-methylbenzene (3ac):

[0030]

[0031] Add 0.25mmol of p-methoxyphenylacetylene, 1mmol of o-toluenesulfonyl hydrazide, 2 equivalents of tetrabutylammonium iodide and 2 equivalents of potassium tert-butoxide to a 25mL three-necked flask, add 18mL of acetonitrile and water The mixed solution was dissolved, and the reticulated vitreous carbon RVC was used as the anode, and the platinum sheet was used as the cathode, and the stirring reaction was carried out under the conditions of 1.4V constant voltage, oxygen atmosphere, and 60°C for 3 hours, and the reaction progress was monitored by TLC. The mixture was extracted with ester, and the organic layer was washed with anhydrous MgSO 4 Drying, the solvent was spin-dried under reduced pressure, and passed through column chromatography (SiO 2 , ethyl acetate / petroleum ether=1:15) to obtain 3ac as a white solid.

[0032] The product is characterized...

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Abstract

The invention discloses a method for synthesizing alkyne sulfone compounds with terminal alkyne and sulfonyl hydrazide. This method synthesizes a series of alkynyl sulfone compounds through the oxidative cross-coupling reaction of terminal alkynes and sulfonyl hydrazides. Functional group tolerance and other advantages. The compounds synthesized by this method were screened for anti-tumor activity in vitro, and the experimental results showed that most of the compounds had strong inhibitory activity on tumor cells.

Description

technical field [0001] The invention relates to chemical synthesis, in particular to a method for synthesizing acetylenic sulfone compounds from terminal alkynes and sulfonyl hydrazides under electrochemical conditions. Background technique [0002] Organic sulfone compounds widely exist in natural products and drug molecules, and play an important role in organic chemistry. Alkyne sulfone compounds are important organic sulfone compounds. They not only have good pharmacological activity, but also are important intermediates in the synthesis of many natural products. They can be obtained by addition, cycloaddition and coupling methods. Other valuable compound. [0003] Organic sulfones are an important class of compounds in medicinal chemistry, because they have good biological activities, such as anti-HIV, anti-cancer, anti-fungal and anti-bacterial, etc. Alkynyl sulfones not only have a wide range of pharmacological activities, but also are important synthetic intermedia...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/07C25B3/20A61P35/00
CPCA61P35/00C25B3/00
Inventor 唐海涛潘英明张羽真莫祖煜
Owner GUANGXI NORMAL UNIV
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