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1,3-aryl group substituted pyrazoline whose 5 position contains ester gruop and its liquid phase synthesis method

A kind of pyrazoline liquid, pyrazoline technology, applied in 1 field, can solve the problems such as can not be directly fully utilized, unsatisfactory yield, time-consuming and the like

Inactive Publication Date: 2004-07-28
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nevertheless, not to mention that some of the above methods will use expensive reagents, some give unsatisfactory yields, and the reaction is carried out in multiple steps, which cannot directly fully utilize commercially available starting materials; Potentially effective, but time-consuming and nearly impossible to quickly and easily obtain large quantities of different compounds with the parent structure in high purity

Method used

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  • 1,3-aryl group substituted pyrazoline whose 5 position contains ester gruop and its liquid phase synthesis method
  • 1,3-aryl group substituted pyrazoline whose 5 position contains ester gruop and its liquid phase synthesis method
  • 1,3-aryl group substituted pyrazoline whose 5 position contains ester gruop and its liquid phase synthesis method

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Step 1: Dissolve 15g of polyethylene glycol (PEG4000) with a molecular weight of 4000 in 60ml of dichloromethane, add 4.16ml of trioctylamine, cool in an ice bath, and slowly add 2.45ml of acryloyl chloride dropwise over 2 hours. After the dropwise addition, the ice bath was removed, and the reaction was carried out at room temperature for 24 hours. After the reaction is complete, add 500ml of anhydrous ether and shake until the solution becomes turbid, freeze for 30 minutes, precipitate crystals, filter with suction, wash with anhydrous ether three times, put it in a desiccator, and vacuum dry overnight to obtain 14.9g of acrylate supported on PEG4000.

[0025] Step 2: Under nitrogen protection, add 185 mg of phenylhydrazine hydrochloride, 8 ml of methanol, 0.5 ml of trioctylamine, 133 mg of benzaldehyde, and stir at room temperature for 30 minutes in a 10 ml small flask; then add 281 mg of chloramine T and PEG4000 support 0.5g of acrylate, temperature controlled at 40...

Embodiment 2

[0029] The reaction steps are the same as in Example 1, except that 3.0ml of methacryloyl chloride is used in step 1; the product obtained is 1-phenyl-3-phenyl-5-methyl-5-formic acid methyl pyridyl oxazoline. The purity is 100%, and the yield is 91%.

[0030] 1 H-NMR (500MHZ, CDCl 3 )δ=1.64(s, 3H), 3.31(d, J=16.6Hz, 1H), 3.71(d, J=16.6Hz, 1H), 3.77(s, 3H), 6.88(t, 1H), 7.11( d, J=8.3Hz, 2H), 7.25(d, J=7.3Hz, 2H), 7.40(m, 3H), 7.70(d, J=7.3Hz, 2H).

Embodiment 3

[0032] The reaction steps are the same as in Example 1, except that what is used in step 1 is 3.0ml methacryloyl chloride; the solvent used for crystallization in step 2 is 50ml isopropanol; the aromatic aldehyde added in step 2 is p-methoxy 164 mg of benzaldehyde. The product obtained was 1-phenyl 3-p-methoxyphenyl 5-methyl-5-methyl carboxylate pyrazoline. The purity is 98%, and the yield is 90%.

[0033] 1 H-NMR (500MHZ, CDCl 3 )δ=1.62(s, 3H), 3.27(d, J=16.5Hz, 1H), 3.69(d, J=16.5Hz, 1H), 3.76(s, 3H), 3.84(s, 3H), 6.86( t, 1H), 6.91(d, J=8.7Hz, 2H), 7.10(d, J=7.0Hz, 2H), 7.23(m, 2H), 7.65(d, J=7.0Hz, 2H).

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Abstract

The present invention discloses a kind of 1,3-aryl substituted pyrazoline whose delta-position contains ester group and its liquid phase synthesis method. In the organic solvent, in the presence of alkali the substituted acryloyl chlorine is coupled on the soluble resin, under the action of organic alkali the isoequivalent aromatic aldehyde and aromatic hydrazine hydrochloride are mixed to obtain the correspondent hydrazone, then the substituted acrylic ester loaded by soluble resin and oxidant are added, and the above-mentioned materials are undergone the ring-forming reaction of one-pot method so as to obtain the 1,3-aryl substituted pyrazoline whose delta-position contains ester group which is loaded on the resin. In the alcohol solvent and under the catalysis of correspondent alcohol sodium the pyrazoline can be separated from soluble resin so as to obtain the invented product with high yield rate and high purity. It can be developed into medicine, pesticide and light sensitive material.

Description

technical field [0001] The invention relates to pyrazoline and a synthesis method thereof, in particular to a 1,3-aryl-substituted pyrazoline containing an ester group at the 5-position and a liquid phase synthesis method thereof. Background technique [0002] Pyrazoline is one of the most common structural components in natural products, photosensitive materials, modern drugs and pesticides, and has a variety of important physiological activities. For example, antibacterial and anti-inflammatory, antifungal, antitumor, and regulating seed germination and plant growth, etc., have great development and utilization value in photosensitive materials, medicine and pesticides. For a long time, people have been imagining how to establish a molecular library of such compounds, so as to systematically screen for biological activity and determine the structure-activity relationship. However, 1,3-aryl-substituted pyrazolines containing an ester group at the ...

Claims

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Application Information

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IPC IPC(8): C07D231/04C07D231/06C07D231/14
Inventor 林旭锋张健王彦广
Owner ZHEJIANG UNIV
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