Synthesis method of beta-ketosulfone compound

A synthesis method and compound technology, applied in the field of synthesis of β-ketosulfone compounds, can solve the problems of poor activity of terminal alkynes, high price, unfavorable production, etc., and achieve the effects of mild reaction conditions, high atom economy and simple operation

Active Publication Date: 2020-04-28
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, they found in their research that the existing methods cannot be extended to cheap and easy-to-obtain terminal alkynes. The main reason is that the terminal alkynes have poor activity and the intermediates obtained by addition of sulfonyl radicals cannot undergo hydration reactions.
Therefore, they used expensive alkynoic acid as a reactant, and the catalyst is difficult to recover, which is not conducive to production

Method used

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  • Synthesis method of beta-ketosulfone compound
  • Synthesis method of beta-ketosulfone compound
  • Synthesis method of beta-ketosulfone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Add 0.5mmol p-nitroaryltetrafluoroborate diazonium salt, 0.6mmolDABCO·(SO 2 ) 2 , add 0.4mmol of phenylacetylene, add 2ml of acetonitrile aqueous solution, (acetonitrile: water = 1:1v / v), add 10mg of mesoporous carbon nitride, add a rotor, pour in oxygen, and stir magnetically at room temperature and under the irradiation of a 250-watt xenon lamp The device was stirred for 8h to end the reaction. The reaction product was separated and purified by column chromatography and thin layer chromatography using ethyl acetate and n-hexane as developing solvents (ethyl acetate:n-hexane=1:3), and the product was isolated. The calculated yield was 76%.

Embodiment 2

[0058] Add 0.5mmol p-methoxyaryltetrafluoroborate diazonium salt, 0.6mmolDABCO·(SO 2 ) 2 , add 0.4mmol phenylacetylene, add 2ml of acetonitrile solution (acetonitrile: water = 1:1), add rotor, add 10mg of mesoporous carbon nitride, add rotor, pour in oxygen, and stir magnetically at room temperature and under the irradiation of a 250-watt xenon lamp The device was stirred for 8h to end the reaction. The reaction product was separated and purified by column chromatography and thin layer chromatography using ethyl acetate and n-hexane as developing solvents (ethyl acetate:n-hexane=1:3), and the product was isolated. The calculated yield was 78%.

Embodiment 3

[0059] The influence of embodiment 3 visible light on synthesis

[0060] Add 0.5mmol p-nitroaryltetrafluoroborate diazonium salt, 0.6mmolDABCO (SO2) 2 in a 25ml pressure-resistant reaction tube, add rotor, add 0.4mmol phenylacetylene, add 2ml acetonitrile aqueous solution, (acetonitrile: water = 1:1 v / v), add 10 mg of mesoporous carbon nitride, add a rotor, pour in oxygen, stir with a magnetic stirrer at room temperature for 8 hours, no target product sulfone is formed.

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Abstract

The invention discloses a synthesis method of a beta-ketosulfone compound, and belongs to the technical field of chemical synthesis. According to the synthesis method, tetrafluoroborate diazonium salt, alkyne and DABCO. (SO2) 2 are subjected to an oxidation bifunctionalization reaction to prepare the beta-ketosulfone compound. The method comprises the following steps: adding DABCO.( SO2) 2, alkyneand tetrafluoroborate diazonium salt which are used as reactants and mesoporous carbon nitride, an organic solvent, water and oxygen which are used as catalysts into a reactor, and stirring for 6-10hours at room temperature under the irradiation of visible light. The method is mild in reaction condition, simple to operate and high in atom economy, and the catalysts can be recycled.

Description

technical field [0001] The invention relates to a synthesis method of a β-ketosulfone compound, belonging to the technical field of chemical synthesis. Background technique [0002] Designing efficient and environmentally friendly methods to construct sulfonyl units has always been a research hotspot in organic chemistry. β-Ketosulfones are an important class of sulfonyl compounds, which are widely used in the fields of medicine, biopharmaceuticals, and materials science. Such compounds exhibit a wide range of biological properties, including antifungal, antibacterial and non-nucleoside inhibitory properties. Therefore, it is of great significance to develop synthetic methods for β-ketosulfones. [0003] The traditional synthesis method of β-ketosulfone mainly adopts the alkylation reaction of benzoyl chloride and sodium sulfonate. The reagents used in this method are highly corrosive, and the substrate range is narrow, the yield is low, and the reaction conditions are rel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/24C07C315/00C07D213/71C07D333/22C07J1/00
CPCC07C315/00C07D213/71C07D333/22C07J1/0051C07C317/24Y02P20/584
Inventor 韩金娥钮腾飞章斌斌
Owner JIANGNAN UNIV
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