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4-sulfonyl pyrolidone compound and synthesis method thereof

A technology of sulfonylpyrrolidone and its synthesis method, which is applied in the direction of organic chemistry, can solve problems such as difficult industrial preparation, and achieve good guiding significance and application prospects

Inactive Publication Date: 2019-12-20
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of traditional sulfonyl compounds requires the use of strong acidic raw materials, which is difficult for large-scale industrial preparation

Method used

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  • 4-sulfonyl pyrolidone compound and synthesis method thereof
  • 4-sulfonyl pyrolidone compound and synthesis method thereof
  • 4-sulfonyl pyrolidone compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019]

[0020] Add 0.2 mmol of N,4-diphenylpenta-2,3-dienamide, 0.2 mmol of DABCO (SO 2 ) 2 , 0.3mmol of p-tolyl diazonium salt, plug the reaction tube with a stopper and place it in high-purity nitrogen or argon to replace the gas, so that the system is in anaerobic condition, then add 2mL of 1,2-dichloroethane, in Place in a 30°C oil bath and stir until the reaction is complete. The reaction solution was directly concentrated under reduced pressure and separated by column chromatography, using a mixture of petroleum ether and ethyl acetate as the mobile phase to obtain the corresponding 5-methyl-1,5-diphenyl-4-toluenesulfonyl -1,5-dihydro-2H-pyrrol-2-one compound example 1.

[0021] Structural characterization of compound example 1: 1 H NMR (400MHz, CDCl 3 )δ7.34-7.24(m, 5H), 7.21-7.11(m, 5H), 7.10-7.02(m, 3H), 6.96(s, 1H), 6.67(s, 1H), 2.36(s, 3H) , 2.20(s, 3H); 13 C NMR (101MHz, CDCl 3 )δ (ppm) 162.2, 157.0, 145.0, 136.8, 135.7, 132.2, 129.5, 128.6, 128.3, 127.9...

Embodiment 2

[0023]

[0024] Add 0.2 mmol of N,4-diphenylpenta-2,3-dienamide, 0.2 mmol of DABCO (SO 2 ) 2 , 0.3mmol of phenyldiazonium salt, stop the reaction tube with a stopper, and place it in high-purity nitrogen or argon to replace the gas, so that the system is in anaerobic condition, then add 2mL of 1,2-dichloroethane, and place Stir in an oil bath at 30°C until the reaction is complete. The reaction solution was directly concentrated under reduced pressure, and separated by column chromatography, using a mixture of petroleum ether and ethyl acetate as the mobile phase to obtain the corresponding 5-methyl-1,5-diphenyl-4-(phenyl Sulfonyl)-1,5-dihydro-2H-pyrrol-2-one compound example 2.

[0025] Structural characterization of compound example 2: 1 H NMR (400MHz, CDCl 3) δ (ppm) 7.55-7.47 (m, 4H), 7.42-7.36 (m, 4H), 7.27 (d, J = 6.5Hz, 3H), 7.14-7.09 (m, 3H), 7.00-6.92 (m, 1H), 4.96(s, 1H), 2.03(s, 3H); 13 C NMR (101MHz, CDCl 3 )δ (ppm) 168.8, 157.0, 143.3, 140.7, 137.6, 133....

Embodiment 3

[0027]

[0028] Add 0.2 mmol of N,4-diphenylpenta-2,3-dienamide, 0.2 mmol of DABCO (SO 2 ) 2 , 0.3mmol of 4-methoxyphenyl diazonium salt, plug the reaction tube with a stopper and place it in high-purity nitrogen or argon to replace the gas, so that the system is in anaerobic condition, then add 2mL of 1,2-dichloro Ethane, placed in an oil bath at 30°C and stirred until complete reaction. The reaction solution was directly concentrated under reduced pressure, and separated by column chromatography, using a mixture of petroleum ether and ethyl acetate as the mobile phase to obtain the corresponding 4-((4-methoxyphenyl)sulfonyl)-5- Example 3 of methyl-1,5-diphenyl-1,5-dihydro-2H-pyrrol-2-one compound.

[0029] Structural characterization of compound example 3: 1 H NMR (400MHz, CDCl 3 )δ (ppm) 7.36-7.29 (m, 3H), 7.26 (d, J=5.9Hz, 2H), 7.22-7.13 (m, 5H), 7.12-7.05 (m, 2H), 6.94 (s, 1H) , 6.68(t, J=7.7Hz, 2H), 3.80(d, J=3.1Hz, 3H), 2.17(d, J=5.3Hz, 3H); 13 C NMR (101MHz, C...

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Abstract

The invention belongs to the technical field of organic chemistry and particularly relates to a preparation method of a 4-sulfonyl pyrolidone compound. The structure of the compound is characterized and confirmed by 1H nuclear magnetic resonance (NMR), 13C NMR and other methods. According o the method, 1,2-dichloroethane is used as a solvent, a metal catalyst is not needed, and a reaction is carried out on an aryl diazo salt and a sulfur dioxide solid substitute at 30 DEG C to obtain sulfonyl free radicals; and cyclization is carried out on the sulfonyl free radicals and 2,3-diene amide to obtain the 4-sulfonyl pyrolidone compound. The preparation method of the 4-sulfonyl pyrolidone compound has the advantages of mild conditions, simplicity and high efficiency, high reaction yield, wide application range of substrates, good product purity and convenience for separation and purification, and has a good application value.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a 4-sulfonyl pyrrolone compound and a synthesis method thereof. Background technique [0002] 1,5-dihydro-2H-pyrrol-2-one (γ-lactam) is an important class of compounds, which widely exist in natural products and biological compounds, especially clinical therapeutic drugs, such as (R)-Rolipram is An antidepressant [(a) J. Zhu, E. Mix, B. Winblad, CNS Drug Rev. 2001, 7, 387; (b) A.L.L. Garcia, M.J.S. Carpes, A.C.B.M.de Oca, M.A.G. dos Santos, C.C. Santana , C.R.D.Correia, J.Org.Chem.2005, 70, 1050]; Brivaracetam is an antiepileptic drug (M.A. Rogawski, Epilepsy Res. 2006, 69, 273). In addition, γ-amino acids, the ring-opening products of γ-lactams, are key intermediates in organic synthesis and are used to synthesize various natural products and pharmaceutical molecules [(a) M. C. Cativiela, I. Romero-Estudillo, Tetrahedron: Asymmetry2016, 27, 999; (b) M. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/38
CPCC07D207/38
Inventor 吴劼叶盛青周凯达蒋华江
Owner TAIZHOU UNIV