Method for synthesizing alkyne sulfone compounds from terminal alkyne and sulfonyl hydrazine

A terminal alkyne, sulfonyl hydrazide technology, applied in the field of chemical synthesis

Active Publication Date: 2020-05-12
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Method for synthesizing alkyne sulfone compounds from terminal alkyne and sulfonyl hydrazine
  • Method for synthesizing alkyne sulfone compounds from terminal alkyne and sulfonyl hydrazine
  • Method for synthesizing alkyne sulfone compounds from terminal alkyne and sulfonyl hydrazine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation and characterization of 1-methoxy-4-(tosylethynyl)benzene (3aa):

[0022]

[0023] 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.

[0024] The product is characterized by:

[0025] Pal...

Embodiment 2

[0027] Preparation and characterization of 1-methoxy-4-((benzenesulfonyl)ethynyl)benzene (3ab):

[0028]

[0029] 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.

[0030] The product is characterized by:

[0031] Yellow oil...

Embodiment 3

[0033] Preparation and characterization of 1-(((4-methoxyphenyl)ethynyl)sulfonyl)-2-methylbenzene (3ac):

[0034]

[0035] 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.

[0036] The product is characterized...

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Abstract

The invention discloses a method for synthesizing alkyne sulfone compounds from terminal alkyne and sulfonyl hydrazine. According to the method, a series of the alkynyl sulfone compounds are synthesized through an oxidative cross-coupling reaction of terminal alkyne and sulfonyl hydrazine, and the method does not need pre-functionalization of alkyne, and has the advantages of high atom economy, nometal or oxidant, good functional group tolerance and the like. The compounds synthesized by the method are subjected to in-vitro antitumor activity screening, and experimental results show that mostof the compounds have relatively 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 Applications(China)
IPC IPC(8): C25B3/00A61P35/00
CPCA61P35/00C25B3/00
Inventor 唐海涛潘英明张羽真莫祖煜
Owner GUANGXI NORMAL UNIV
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