Method for preparing antiseptic triaryl-2-pyrazoline derivative by microwave

A technology of derivatives and fungicides, which is applied in the field of microwave synthesis of fungicides triaryl-2-pyrazoline derivatives, can solve the problems of difficult separation and purification, incomplete reaction, difficult homogeneous reaction, etc. The effect of convenient processing, improved reaction yield and high reaction selectivity

Inactive Publication Date: 2009-11-18
ZHEJIANG UNIV
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Problems solved by technology

[0009] The method for cyclizing 2-pyrazoline derivatives by α, β-unsaturated carbonyl compounds, hydrazine and derivatives thereof is used for α, α'-dibenzylidene cyclohexanone derivatives and phenylhydrazine derivatives As the main raw material, when synthesizing triaryl-2-pyrazoline derivatives with α-benzylidene cyclohexapyrazoline ring structure, it was found that the synthesis of α-benzylidene cyclohexapyrazoline rings Although the triaryl-2-pyrazoline derivatives of the structure can obtain products, the conventional heating method, due to the long-term heating and reflux under strong alkali conditions, makes the more sensitive double α, β-unsaturated carbonyl structure α,α'-Dibenzylidene cyclohexanone derivatives are easily decomposed and oxidized, so the reaction is incomplete, the yield is low, the post-treatment process is complicated, and it is difficult to separate and purify
[0010] The α, α'-dibenzylidene cyclohexanone deri

Method used

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  • Method for preparing antiseptic triaryl-2-pyrazoline derivative by microwave
  • Method for preparing antiseptic triaryl-2-pyrazoline derivative by microwave
  • Method for preparing antiseptic triaryl-2-pyrazoline derivative by microwave

Examples

Experimental program
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Effect test

Embodiment 1

[0047] α, α'-dibenzylidene cyclohexanone is reacted with phenylhydrazine, and a triaryl-2-pyrazoline derivative (c) is synthesized under a conventional heating method.

[0048] In a 100ml three-neck flask, add 30ml of absolute ethanol, 3mmol α,α'-dibenzylidene cyclohexanone, heat, stir and dissolve, then add 6mmol of phenylhydrazine, 6mmol of sodium ethoxide, heat and reflux for 8 hours, and track the reaction to equilibrium by TLC . The reaction system was cooled in ice water, and a yellow solid precipitated out. The solid was filtered with suction and dried to obtain a crude product, which was recrystallized from methanol / dichloromethane to obtain a pure product. Yield: 72%.

[0049] C 26 h 24 N 2 , yellow solid, mp: 143-145°C, IR (KBr, cm -1 )3447, 3054, 2933, 2863, 1598, 1501, 1489, 1091, 1013. 1 HNMR (CDCl 3 , δppm) 1.44(1H, m), 1.65(1H, m), 1.91(1H, m), 2.19(1H, m), 2.42(1H, t), 2.98(1H, m), 3.03(1H, t ), 4.57 (1H, d), 6.81 (1H, t), 7.04 (2H, d), 7.15 (2H, t), 7....

Embodiment 2

[0051] α, α'-dibenzylidene cyclohexanone is reacted with phenylhydrazine, and the triaryl-2-pyrazoline derivative (c) is synthesized under the method of microwave radiation.

[0052]In a 150ml flask for microwave reaction, add 30ml absolute ethanol, 3mmol α, α'-dibenzylidene cyclohexanone, 6mmol phenylhydrazine, 6mmol sodium ethoxide, and react in a microwave oven with a microwave radiation power of 250W After 5 minutes, TLC followed the detection reaction to equilibrium. After the reaction was complete, the reaction system was cooled in ice water and a yellow solid precipitated out. The solid was filtered with suction and dried to obtain a crude product, which was recrystallized from methanol / dichloromethane to obtain a pure product. Yield: 98%. Compound characterization is the same as in Example 1.

Embodiment 3

[0054] α, α'-dibenzylidene cyclohexanone is reacted with phenylhydrazine, and a triaryl-2-pyrazoline derivative (c) is synthesized under the method of secondary microwave radiation.

[0055] In a 150ml flask used for microwave reaction, add 30ml absolute ethanol, 3mmol α, α'-dibenzylidene cyclohexanone, 6mmol phenylhydrazine, 6mmol sodium ethoxide, and react 5 Minutes, let the reaction mixture cool down to room temperature (20-25° C.), and then carry out the second microwave irradiation reaction. The reaction time of the second microwave radiation reaction was the same as that of the first microwave radiation reaction. Under the microwave radiation power of 250W, the reaction was carried out for 5 minutes, and the TLC tracking detection reaction reached equilibrium. After the reaction was complete, the reaction system was cooled in ice water and a yellow solid precipitated out. The solid was filtered with suction and dried to obtain a crude product, which was recrystallized fr...

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Abstract

The invention relates to a method for preparing antiseptic triaryl-2-pyrazoline derivative by microwave, which is characterized by taking alpha, alpha'-dibenzyl cyclohexanone derivative having alpha, beta-unsaturated carboxide structure and phenyl hydrazine derivative as main raw materials; the raw materials react for 5-10min in sodium alcoholate and alcohol solution under the condition that the microwave power is 200-500W to be directly cyclized and synthesized to be the antiseptic triaryl-2-pyrazoline derivative which maintains one double-bond and has alpha-benzal cyclohexyl and pyrazoline ring structure. Therefore, the method has the advantages of high reaction selection, production rate and purity of the product, easy purification, etc.

Description

technical field [0001] The present invention relates to a kind of synthesis method of triaryl-2-pyrazoline derivatives (Triaryl-2-pyrazoline derivatives) of microwave synthesis bactericide, specifically relate to have double α, β- unsaturated carbonyl structure α, α'- Dibenzylidene cyclohexanone derivatives and phenylhydrazine derivatives are used as main raw materials to directly cyclize fungicide triaryl-2-pyrazoline derivatives by cyclization under the condition of microwave radiation. Background technique [0002] Pyrazoline is an extremely important nitrogen-containing five-membered heterocyclic compound. It is reported that most pyrazolines and derivatives thereof have strong biological activity, such as antibacterial [Khali H Z, Yanni S.A.Synthesis of NewAnilido-Pyrazoline and Isoxazoline Derivatives.J.Indian.Chem.Soc., 1981 , 58, 168-170.], antiviral [Rawal A A., Thakor V M, Shah N M.Synthesis of Some 1,3,5-Triphenylpyrazolines and 3,5-Diphenyl-cyclohexen-1-ones.J.I...

Claims

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Application Information

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IPC IPC(8): C07D231/54C07D231/56B01J19/12A01N43/56A01P3/00
Inventor 徐伟亮徐子河柴灵芝
Owner ZHEJIANG UNIV
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