Synthesizing method of benzofuranone compound containing sulfonyl

A technology of benzofuranone and synthesis method, which is applied in directions such as organic chemistry and achieves the effects of mild conditions, safe operation and wide range of substrates

Active Publication Date: 2016-10-26
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, most of the methods for synthesizing benzofuranone compounds are realized by intermolecular multicomponent reactions, which can be realized by transition metal catalysis (such as copper, gold, palladium, iron, etc.) (Y.Liu, J. Qian, S. Lou, and Z. Xu, J. Org. Chem. 2010, 75, 6300–6303, J.-P. Wan, H. Wang, Y. Liu, and H. Ding, Org. Lett. 2014, 16,5160-5163), and by metal-free catalysis (X.-C.Huang, Y.-L.Liu, Y.Liang, S.-F.Pi, F.Wang, and J.- H.Li, Org.Lett.2008,10,1525-1528), it has been reported recently that the addition and cyclization of phenyl-linked 1,6-enynes by free radicals is realized (M.Hu, R .-J.Song, and J.-H.Li, Angew.Chem.Int.Ed.2015,54,608–612), and the addition of phenyl-linked 1,6-enynes to phenyl-linked 1,6-enynes with silver as a catalyst The method for constructing benzofuranone through cyclization cascade reaction has not been reported in the literature yet.

Method used

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  • Synthesizing method of benzofuranone compound containing sulfonyl
  • Synthesizing method of benzofuranone compound containing sulfonyl
  • Synthesizing method of benzofuranone compound containing sulfonyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add 0.3 mmol 2-(4-methylphenylethynyl) phenyl alkenyl ether (M.Hu, R-J.Song and J-H, Li, Angew.Chem.Int.Ed.2015,54,608– 612), 0.6 mmol of sodium benzene sulfinate, 0.06 mmol of silver nitrate, 0.6 mmol of potassium persulfate and 3 milliliters of acetonitrile, stirred and reacted at 80 degrees Celsius at 700 rpm for 4 hours, and stopped stirring. Add 4 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous magnesium sulfate to dry, filter, evaporate the solvent under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The eluent was petroleum ether: ethyl acetate mixed solvent with a volume ratio of 8:1, and the yield was 74%.

[0034] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows figure 1 and figure 2 shown; the structural characterization data are shown below:

[0035] 1 H NMR (400MHz, CDCl ...

Embodiment 2

[0042]Add 0.3 mmol 2-thienylphenyl alkenyl ether (M.Hu, R-J. Song and J-H, Li, Angew. Chem. Int. Ed. 2015, 54, 608–612), 0.6 mmol phenylene oxide into the reaction tube Sodium sulfonate, 0.06 mmol of silver nitrate, 0.6 mmol of potassium persulfate and 3 ml of acetonitrile were stirred and reacted at 80 degrees Celsius at 700 rpm for 6 hours, and the stirring was stopped. Add 4 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous magnesium sulfate to dry, filter, evaporate the solvent under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The eluent was petroleum ether:ethyl acetate mixed solvent with a volume ratio of 5:1, and the yield was 62%.

[0043] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows image 3 and Figure 4 shown; the structural characterization data are shown below:

[0044] 1 H ...

Embodiment 3

[0051] Add 0.3 mmol 5-chloro-2-phenylethynylphenyl alkenyl ether (M.Hu, R-J. Songand J-H, Li, Angew. Chem. Int. Ed. 2015, 54, 608–612), 0.6 Millimole sodium benzenesulfinate, 0.06 mmol silver nitrate, 0.6 mmol potassium persulfate and 4 milliliters of acetonitrile were stirred and reacted at 80 degrees Celsius at 700 rpm for 4 hours, and the stirring was stopped. Add 4 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous magnesium sulfate to dry, filter, evaporate the solvent under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The eluent was petroleum ether:ethyl acetate mixed solvent with a volume ratio of 6:1, and the yield was 62%.

[0052] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows Figure 5 and Figure 6 shown; the structural characterization data are shown below:

[0053] 1 H NMR (400...

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Abstract

The invention belongs to the technical field of organic synthesizing and discloses a synthesizing method of a benzofuranone compound containing sulfonyl. The synthesizing method includes: adding substrate with the structure shown in formula 1, sodium sulfinate, silver salt catalyst, oxidizing agent and solvent into a reactor, performing stirring reaction under 80-90 DEG C, and separating and purifying reaction products to obtain the benzofuranone compound containing sulfonyl. The synthesizing method has the advantages that the sodium sulfinate which is simple and easy to obtain is used as the sulfonyl source, the cheap silver salt is used as the catalyst, the oxidizing agent is mild and free of environment pollution, and the functional benzofuranone compound containing sulfonyl is synthesized; the method has innovativeness and atom economy, is mild in condition and safe to operate and has potential practical value.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of a sulfone group-containing benzofuranone compound. Background technique [0002] Organic sulfone compounds are important intermediates in agricultural chemistry and medicinal chemistry. Their unique structural properties have attracted high attention in recent years, especially the synthesis of sulfone-based organic molecules with pharmaceutical and biological activities is a research hotspot in the field of organic drug synthesis. , such as anti-HIV-1, SR 33805oxalate. According to literature reports, the introduction of sulfone groups into organic frameworks is often achieved through transition metal (such as Pd, Cu, Fe, etc.) catalyzed coupling to construct C(sp 2 )-S or C(sp 3 )-S to achieve. (C. Chen, J. Su, X. Tong, Chem. Eur. J., 2013, 19, 5014-5018; X. Zeng, E, Nakamura, Org. Lett., 2012, 14, 954-956.) But among them The sou...

Claims

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Application Information

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IPC IPC(8): C07D307/80C07D409/06
CPCC07D307/80C07D409/06
Inventor 伍婉卿易松健江焕峰
Owner SOUTH CHINA UNIV OF TECH
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