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A green method for the synthesis of 1,3,5-trisubstituent-2-pyrazoline derivatives catalyzed by ionic liquids

An ionic liquid, tri-substituted technology, applied in chemical instruments and methods, chemical/physical processes, physical/chemical process catalysts, etc., can solve the problems of long reaction time, low yield, complicated post-processing, etc., and reduce the reaction time. , reduced usage, easy post-processing effects

Inactive Publication Date: 2017-03-22
SHANDONG NORMAL UNIV
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Problems solved by technology

Among them, many catalysts have been reported, such as: sodium acetate, acetic acid, sodium hydroxide, sodium bisulfate, etc., and the reaction methods include ordinary heating, microwave, high-speed ball milling technology, ultrasonic technology, etc., and most reactions have reaction time. Long, low yield, complex post-processing and other issues

Method used

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  • A green method for the synthesis of 1,3,5-trisubstituent-2-pyrazoline derivatives catalyzed by ionic liquids
  • A green method for the synthesis of 1,3,5-trisubstituent-2-pyrazoline derivatives catalyzed by ionic liquids
  • A green method for the synthesis of 1,3,5-trisubstituent-2-pyrazoline derivatives catalyzed by ionic liquids

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of 1-sulfonic acid butyl-3-methylimidazolium triflate:

[0025] Take 6.8g (0.05mol) of 1,4-sultone and 4.0g (0.05mol) of N-methylimidazole in a round bottom flask, stir at room temperature for 24h, and wash the solid product with diethyl ether and toluene to remove residual The raw material impurities of the reaction were then vacuum-dried, then added 7.5g (0.05mol) trifluoromethanesulfonic acid and stirred at 40°C for 2h to generate 1-sulfonic acid butyl-3-methylimidazole trifluoromethanesulfonate, liquid phase The product was repeatedly washed with toluene and ether to remove non-ionic impurities, and then vacuum-dried to obtain a relatively pure ionic liquid product.

[0026] The physical properties and spectral data of the obtained compound are as follows: δ H 9.161(s,1H),7.78(s,1H),7.748(s,1H),4.210(t,J=7.2,2H),3.89(s,3H),2.68(t,J=7.2,2H), 1.90 (q, J = 7.6, 2H), 1.61 (q, J = 4.6, 2H).

Embodiment 2

[0028] 1,3-Diphenyl-5-(4-dimethylaminophenyl)-2-pyrazoline

[0029] Take 0.25g (1mmol) 1-phenyl-3-(4-dimethylaminophenyl)-2-propenyl-1-one, 0.14g (1.3mmol) phenylhydrazine and 2mL ionic liquid 1-sulfonic acid butyl -3-Methylimidazole trifluoromethanesulfonate was dissolved in a two-necked round-bottomed flask by ultrasonic vibration, connected to a reflux device, and stirred at a temperature of 50°C for 0.5h (TLC tracking and monitoring of the reaction), the reaction solution was cooled and filtered with suction An orange-yellow solid was obtained, which was then recrystallized from ethanol to obtain 1,3-diphenyl-5-(4-dimethylaminophenyl)-2-pyrazoline as yellow needle crystals. The yield was 0.30 g, and the yield was 89.4%. .

[0030] The physical properties and spectral data of the obtained compound are as follows: mp 108-109°C, δ H 7.72(d,J=6.0Hz,2H),7.32~7.44(m,3H),7.00~7.16(m,6H),6.64~6,71(m,3H),5.29(dd,J 1 =6.0Hz,J 2 =12.0Hz,1H),3.78(dd,J 1 =12.0Hz,J 2 =18.0Hz,1H),...

Embodiment 3

[0032] 1-phenyl--3-(4-methylphenyl)-5-(3-azidophenyl)-2-pyrazoline

[0033] Take 0.27g (1mmol) 1-(4-methylphenyl)-3-(3-azidophenyl)-2-propenyl-1-one, 0.14g (1.3mmol) phenylhydrazine and 2mL ionic liquid 1-Sulphonic acid butyl-3-methylimidazolium trifluoromethanesulfonate was dissolved in a two-necked round-bottomed flask by ultrasonic vibration, connected to a reflux device, and the temperature was controlled at 50°C to stir and react for 1 h (TLC tracking and monitoring the reaction), and the reaction Liquid cooling, suction filtration to obtain orange solid powder, and then recrystallized with ethanol to obtain orange needle-like crystal 1-phenyl-3-(4-methylphenyl)-5-(3-azidophenyl) -2-pyrazoline, yield 0.31 g, yield 85.0%.

[0034] The physical properties and spectral data of the obtained compound are as follows: mp 124-126°C, δ H 7.61(d, J=9.0Hz, 2H), 7.37(t, J=9.0Hz, 1H), 6.97~7.24(m, 9H), 6.71(t, J=6.0Hz, 1H), 5.44(dd,J 1 =6.0Hz,J 2 =12.0Hz,1H),3.83(dd,J 1 =12.0Hz,...

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Abstract

The invention relates to an environmental-friendly method for catalytic synthesis of a 1,3,5-triple substituent-2-pyrazoline derivative through ionic liquid. The method comprises the following steps: mixing a chalcone derivative, a substituted hydrazine and an ionic liquid catalyst under solvent-free conditions, ultrasonically oscillating and dissolving, heating, refluxing, stirring and reacting at the temperature of 50-60 DEG C for 0.5-1 hour, cooling, filtering and recrystallizing the reaction solution, thereby obtaining the product, wherein the molar ratio of the chalcone derivative to the substituted hydrazine to the ionic liquid catalyst is 1:(1.2-1.5):(3-6). According to the preparation method disclosed by the invention, a solvent is not needed, the reaction time is reduced by a half, the reactants are synthesized under the catalysis action of the functional ionic liquid, the functional ionic liquid can be recycled, use of an organic reagent is greatly reduced, the reaction temperature is reduced from the original about 110 DEG C to about 50 DEG C, the aftertreatment is relatively simple, and energy conservation and high efficiency of environment-friendly chemical synthesis can be realized.

Description

technical field [0001] The invention relates to a new method for synthesizing 1,3,5-trisubstituent-2-pyrazoline derivatives, belonging to the technical field of chemical synthesis. Background technique [0002] 2-Pyrazoline compounds are an important class of nitrogen-containing heterocyclic compounds, and their derivatives have good physiological and pharmacological activities in pesticides and medicines, including antibacterial, antidepressant, anticonvulsant, antiviral, anti-tuberculosis, Inhibit immunity, insecticide and herbicide, among which 1-acetyl-3,5-diaryl-2-pyrazoline derivatives can inhibit the synthesis of monoamine converting enzymes. Therefore, the synthesis and application of 1,3,5-trisubstituent-2-pyrazoline have attracted widespread attention. On the other hand, pyrazoline compounds are also widely used in the field of optoelectronics because of their strong fluorescence, especially in optical brighteners and dyes for paper materials and textiles, especia...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/06B01J31/02
Inventor 刘庆俭隋雪燕
Owner SHANDONG NORMAL UNIV
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