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Synthesis method of gamma-keto sulfone compound

A synthesis method and compound technology, applied in the field of synthesis of γ-ketosulfone compounds, can solve problems such as limiting the scope of application of substrates, achieve good guiding significance, application prospects, and mild reaction conditions

Active Publication Date: 2020-11-13
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

All of the above synthetic methods require the use of oxidizing agents or metal catalysts, which limits the scope of application of the substrates for this type of reaction

Method used

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  • Synthesis method of gamma-keto sulfone compound
  • Synthesis method of gamma-keto sulfone compound
  • Synthesis method of gamma-keto sulfone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] Add 0.4 mmol of 2-vinylpyridine, 0.6 mmol of 1-phenylcyclopropanol and 0.8 mmol of DABCO·(SO 2 ) 2 , seal the reaction tube with a stopper, replace the gas in high-purity nitrogen, make the system in anaerobic condition, add 2mL of acetonitrile, and stir in an oil bath at 40°C until the reaction is complete. The reaction solution was directly concentrated under reduced pressure, and separated by column chromatography, using a mixture of dichloromethane and methanol as the mobile phase to obtain the corresponding compound example 1.

[0022] Structural characterization of compound example 1: 1 H NMR (400MHz, CDCl 3 )δ8.52(d,J=3.1Hz,1H),7.97(m,2H),7.69–7.57(m,2H),7.49(m,2H),7.27(s,1H),7.18(dd,J =7.1,5.1Hz,1H),3.67–3.52(m,4H),3.44–3.32(m,4H); 13 C NMR (100MHz, CDCl 3 )δ195.66, 157.00, 149.50, 136.90, 135.76, 133.86, 128.83, 128.14, 123.48, 122.17, 52.39, 47.85, 30.84, 30.14; HRMS (ESI): m / z [M+H] + calcd for C 16 h 18 NO 3 S + :304.1007; found: 304.10...

Embodiment 2

[0024]

[0025] Add 0.2 mmol of 4-vinylpyridine, 0.3 mmol of 1-phenylcyclopropanol and 0.4 mmol of DABCO.(SO 2 ) 2 , seal the reaction tube with a stopper, replace the gas in high-purity nitrogen, make the system in anaerobic condition, add 1mL of acetonitrile, and stir in an oil bath at 40°C until the reaction is complete. The reaction solution was directly concentrated under reduced pressure, and separated by column chromatography, using a mixture of dichloromethane and methanol as the mobile phase to obtain the corresponding compound example 2.

[0026] Structural characterization of compound example 2: 1 H NMR (400MHz, CDCl 3 )δ8.54(d,J=4.2Hz,1H),7.95–7.87(m,2H),7.63–7.54(m,2H),7.46(t,J=7.7Hz,2H),7.38(s,1H ),7.37(s,1H),7.30(t,J=7.5 Hz,2H),7.22(t,J=7.1Hz,2H),7.18–7.08(m,1H),4.79(dd,J=8.1, 5.3Hz,1H),4.56(dd,J=14.6,8.2Hz,1H),3.64(dd,J=14.6,5.3Hz,1H),3.51–3.32(m,2H),3.08–2.90(m,2H ); 13 C NMR (100MHz, CDCl 3 )δ195.55, 159.52, 149.22, 141.27, 137.12, 135.80, 133.77, 1...

Embodiment 3

[0028]

[0029] Add 0.2mmol of 3-methyl-2-vinylpyridine, 0.3mmol of 1-phenylcyclopropanol and 0.4mmol of DABCO.(SO 2 ) 2 , seal the reaction tube with a stopper, replace the gas in high-purity nitrogen, make the system in anaerobic condition, add 1mL of acetonitrile, and stir in an oil bath at 40°C until the reaction is complete. The reaction solution was directly concentrated under reduced pressure, and separated by column chromatography, using a mixture of dichloromethane and methanol as the mobile phase to obtain the corresponding 1-phenyl-3-(3-methylpyridine-2-ethyl ) Example 3 of sulfonyl acetonide compound.

[0030] Structural characterization of compound example 3: 1 H NMR (400MHz, CDCl 3 )δ8.36–8.24(m,1H),8.01–7.93(m,2H), 7.65–7.57(m,1H),7.48(dd,J=16.2,8.5Hz,3H),7.09(dd,J= 7.6,4.8Hz,1H),3.69(dd,J=9.6,5.9Hz,2H),3.64–3.55(m,2H),3.45(dd,J=8.2,6.6Hz,2H),3.37–3.28(m ,2H); 13 C NMR (100MHz, CDCl 3)δ195.71, 155.10, 146.54, 137.82, 135.80, 133.84, 131.59, 128.84, 128...

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Abstract

The invention belongs to the field of organic chemistry, and particularly relates to a synthesis method of gamma-keto sulfone compounds. The structure of the compounds is characterized and confirmed by methods such as 1HNMR, 13CNMR and high-resolution mass spectrometry. According to the method, no metal catalyst is needed, and the gamma-keto sulfone compound is obtained through a reaction of substituted cyclopropanol, a sulfur dioxide substitute and alkenyl pyridine. The synthesis method of the gamma-keto sulfone compound has the advantages of mild conditions, simplicity, high efficiency, highreaction yield, wide substrate application range, high product purity, and convenience in separation and purification and has a high application value.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a synthesis method of gamma-ketosulfone compounds. Background technique [0002] Ketone sulfones are an important class of organic intermediates that can participate in many types of chemical transformations and are also present in many active natural products or drug molecules. There are relatively many reports on β-ketosulfone compounds, which can be used in the synthesis of various important organic compounds such as alkenes, alkenyl sulfones and tetrahydropyrans, while there are relatively few reports on the synthesis methods of γ-ketosulfone compounds. It is mainly obtained by oxidation of sulfide. For example, Armido Studer's research group used mercaptans to nucleophilically substitute halogenated hydrocarbons and then oxidized them with sodium borate to obtain γ-ketosulfone compounds [Xia Y., Studer A., ​​Angew. Chem. Int. Ed., 2019, 58, 9836 .]. ...

Claims

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Application Information

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IPC IPC(8): C07D213/34
CPCC07D213/34
Inventor 叶盛青吴劼张春
Owner TAIZHOU UNIV
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