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Pyrazoline derivative and preparation method thereof

A technology of dihydropyrazoles and derivatives, applied in the direction of organic chemistry, can solve the problems of expensive metal catalysts, limited application, cumbersome steps, etc., and achieve the effects of good universality, simple operation, and single target product

Inactive Publication Date: 2017-10-20
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of reaction requires expensive metal catalysts, and the steps are cumbersome, which greatly limits its application.

Method used

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  • Pyrazoline derivative and preparation method thereof
  • Pyrazoline derivative and preparation method thereof
  • Pyrazoline derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: The structure of 5-(azidomethyl)-3-(p-chlorotolyl)-1-toluenesulfonyl-4,5-dihydro-pyrazole is:

[0048]

[0049] Molecular formula: C 17 h 16 ClN 5 o 2 S

[0050] Chinese name: 5-(azidomethyl)-3-(p-chlorotolyl)-1-toluenesulfonyl-4,5-dihydro-pyrazole

[0051] English name: 5-(azidomethyl)-3-(4-chlorophenyl)-1-tosyl-4,5-dihydro-pyrazole

[0052] Molecular weight: 389.0710

[0053] Appearance: yellow solid

[0054] Melting point: 120-122°C

[0055] Proton NMR spectrum: (500MHz, CDCl 3 ):δ7.80-7.75(m,2H),7.58(dd,J=8.5,1.6Hz,2H),7.34(dd,J=8.7,2.1Hz,2H),7.29(d,J=7.9Hz, 2H), 4.05(tdd, J=10.0, 6.0, 3.1Hz, 1H), 3.88(dd, J=12.6, 6.1Hz, 1H), 3.80-3.71(m, 1H), 3.10(dt, J=10.0, 1.1Hz, 2H), 2.38(d, J=1.7Hz, 3H).

[0056] Carbon NMR spectrum: (125MHz, CDCl 3 ): δ156.91, 144.77, 136.86, 131.74, 129.73, 128.96, 128.89, 128.59, 128.21, 60.74, 54.08, 37.37, 21.64.

[0057] Infrared Absorption Spectrum ν max 3043,2925,2853,2105,1600,1450,1355,1290,1170,1090,933,...

Embodiment 2

[0059] Example 2: The structure of 5-(azidomethyl)-3-(m-chlorotolyl)-1-toluenesulfonyl-4,5-dihydro-pyrazole is:

[0060]

[0061] Molecular formula: C 17 h 16 ClN 5 o 2 S

[0062] Chinese name: 5-(azidomethyl)-3-(m-chlorotolyl)-1-toluenesulfonyl-4,5-dihydro-pyrazole

[0063] English name: 5-(azidomethyl)-3-(3-chlorophenyl)-1-tosyl-4,5-dihydro-pyrazole

[0064] Molecular weight: 389.0710

[0065] Appearance: yellow solid

[0066] Melting point: 108-110°C

[0067] Proton NMR spectrum: (500MHz, CDCl 3 ): δ7.79(d, J=8.3Hz, 2H), 7.65(t, J=1.9Hz, 1H), 7.51(dd, J=7.7, 1.4Hz, 1H), 7.41-7.35(m, 1H) ,7.31(t,J=7.7Hz,3H),4.14-4.02(m,1H),3.88(dd,J=12.6,6.1Hz,1H),3.76(dd,J=12.6,3.1Hz,1H), 3.17-3.05(m,2H),2.40(s,3H).

[0068] Carbon NMR spectrum: (125MHz, CDCl 3 ): δ156.59, 144.79, 134.79, 132.23, 131.82, 130.72, 129.96, 129.76, 128.58, 126.89, 125.05, 60.69, 54.09, 37.35, 21.65.

[0069] Infrared Absorption Spectrum ν max 3071,2923,2855,2100,1599,1447,1356,1291,1170,1091,9...

Embodiment 3

[0071] Example 3: The structure of 5-(azidomethyl)-3-(m-bromomethylphenyl)-1-toluenesulfonyl-4,5-dihydro-pyrazole is:

[0072]

[0073] Molecular formula: C 17 h 16 BrN 5 o 2 S

[0074] Chinese name: 5-(azidomethyl)-3-(m-bromomethylphenyl)-1-toluenesulfonyl-4,5-dihydro-pyrazole

[0075] English name: 5-(azidomethyl)-3-(3-bromophenyl)-1-tosyl-4,5-dihydro-pyrazole

[0076] Molecular weight: 433.0206

[0077] Appearance: yellow solid

[0078] Melting point: 121-123°C

[0079] Proton NMR spectrum: (500MHz, CDCl 3 ):δ7.81-7.75(m,3H),7.58-7.49(m,2H),7.30(d,J=8.0Hz,2H),7.24(t,J=7.9Hz,1H),4.06(tdd, J=9.7,6.0,3.2Hz,1H),3.88(dd,J=12.7,6.0Hz,1H),3.74(dd,J=12.6,3.1Hz,1H),3.16-3.04(m,2H),2.39 (s,3H).

[0080] Carbon NMR spectrum: (125MHz, CDCl 3): δ156.56, 144.83, 133.63, 132.45, 131.75, 130.23, 129.78, 129.67, 128.56, 125.51, 122.83, 60.71, 54.06, 37.30, 21.65.

[0081] Infrared Absorption Spectrum ν max 3073,2923,2854,2100,1598,1451,1356,1292,1170,1090,995,854,808,770cm...

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Abstract

The invention aims at providing a pyrazoline derivative and a preparation method thereof. A structural formula of the derivative is shown in the attached figure, wherein R1 is selected from -ClC6H4, -BrC6H4, -NO2C6H4, -t-Bu, -OMeC6H4, -CH3C6H4, and the like; R2 is selected from -Ts and the like. Compared with the existing method of synthesizing the pyrazoline derivative, the method has the advantages that (A) the low-cost and environment-friendly anhydrous copper acetate is used as a catalyst, but the high-cost transition metal catalyst is not used; (B) the reaction can be performed at room temperature, the universality is good, and the yield rate is higher; (C) the experiment operation is simple, the target product is single, and the post-treatment is convenient; the moderate reaction conditions, simple operation, low-cost and easy-obtaining catalyst, and higher yield rate can lay a foundation for the wide application and industrialized production of the pyrazoline derivative.

Description

technical field [0001] The invention relates to a dihydropyrazole derivative and a preparation method thereof. Background technique [0002] Five-membered azacyclic pyrazoles are important compounds with special structures. Due to the potential biological activity of these compounds, their structural units are widely found in natural products, bioactive molecules or pharmaceuticals (a) T.Z.Gulhan, C.Pierre, E.Kevser, Eur.J.Med.Chem., 2000, 35, 635–641; b) M.V. Reddy, V.K. Billa, V.R. Pallela, E.P. Bioorg., Med. Chem., 2008, 16, 3907). For example 2,5,5-trimethyl-1,5,6,10b-tetrahydro-pyrazolo[5,1-a]isoquinoline and 3,5-diphenyl-4,5-dihydro - Pyrazole-1-thiocarboxylic acid amide compounds have good biological activity and can be used as pharmaceutical intermediates (a) B.Asha, B.A.Roouf, A.Amir, Eur.J.Med.Chem., 2009,44 , 1317–1325; b) C. Franco, C. Simone, O. Francisco, Eur. J. Med. Chem., 2010, 45, 800–804). The application fields of pyrazole derivatives are more and mor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/06
CPCC07D231/06
Inventor 郝健康宇飞万文
Owner SHANGHAI UNIV
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