Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A method for preparing 1,3,5-triaryl-substituted pyrazoline derivatives

A pyrazoline and triaryl technology, which is applied in the field of organic chemical synthesis, can solve the problems of great harm to human body and environment, complicated operation process, difficult separation of products, etc., and achieves the effects of cheap raw materials, good selectivity, and overcoming high toxicity.

Inactive Publication Date: 2016-04-20
ZHEJIANG NORMAL UNIVERSITY
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the most commonly used method for synthesizing polyaryl-substituted pyrazoline derivatives is through the addition-condensation reaction of 1,3-dicarbonyl compounds or α,β-unsaturated carbonyl compounds and hydrazine (Org.Lett .2009,11,2097-2100; Org.Lett.2000,2,2833-2836), the raw materials of this reaction are cheap and easy to obtain, but the toxicity of hydrazine is high, which is harmful to human body and environment, and the choice of this reaction The property is poor, and the mixture of two isomers is usually obtained, and the product is difficult to separate; there are reports in the literature that 3-butynol replaces 1,3-dicarbonyl compounds to synthesize N-aryl-substituted pyrazoles regioselectively phenoline, but metal zinc catalysis is required, and the conditions are relatively strict (Org. Lett. 2008, 10, 2377-2379); there are also reports in the literature that halogenated aromatic hydrocarbons, carbon monoxide, arylethene, hydrazine and other raw materials are catalyzed by metal palladium. Synthesis of polyaryl substituted pyrazolines (Eur.J.Org.Chem.2011, 4919-4924), but this method requires the use of noble metal palladium as a catalyst and gaseous carbon monoxide as a raw material, and the operation process is more complicated

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A method for preparing 1,3,5-triaryl-substituted pyrazoline derivatives
  • A method for preparing 1,3,5-triaryl-substituted pyrazoline derivatives
  • A method for preparing 1,3,5-triaryl-substituted pyrazoline derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1: Preparation of 2-(3,5-diphenyl-4,5-dihydropyrazolyl)-N-methylaniline

[0018] The reaction formula is:

[0019]

[0020] At room temperature, add 0.30g (1mmol) 1-methyl-3-benzylbenzotriazole bromide, 0.10g (1mmol) styrene, 25mL tetrahydrofuran (THF) to a 50ml round bottom flask, stir for 10 Minutes later, 0.11 g (1 mmol) of potassium tert-butoxide (t-BuOK) was added, followed by thin-layer chromatography (developing solvent: ethyl acetate:petroleum ether=1:5, volume ratio). After the reaction was completed, THF was concentrated under reduced pressure to recover THF, 10 ml of water and 20 ml of ethyl acetate were added to the residue, and the liquid was separated. Wash with saturated brine, and dry over anhydrous magnesium sulfate. Ethyl acetate was recovered by concentration under reduced pressure, and the residue was quickly separated by column chromatography (eluent: ethyl acetate: petroleum ether = 1:15, volume ratio) to obtain 0.21 g of a yellow soli...

Embodiment 2

[0021] Example 2: Preparation of 2-(3,5-diphenyl-4,5-dihydropyrazolyl)-N-methylaniline

[0022] At room temperature, add 0.30 g (1 mmol) of 1-methyl-3-benzylbenzotriazole bromide, 0.10 g (1 mmol) of styrene, 25 mL of acetonitrile (CH 3 CN), after stirring for 10 minutes, add 0.11g (1mmol) potassium tert-butoxide (t-BuOK), and trace with thin-layer chromatography (developing solvent: ethyl acetate:petroleum ether=1:5, volume ratio). After the reaction is over, concentrate under reduced pressure to recover CH 3 CN, add 10 milliliters of water and 20 milliliters of ethyl acetate to the residue, separate the layers, extract the organic phase with 2×20 milliliters of ethyl acetate, combine the organic layers, wash with 2×20 milliliters of saturated brine, wash with anhydrous magnesium sulfate to dry. Ethyl acetate was recovered by concentration under reduced pressure, and the residue was quickly separated by column chromatography (eluent: ethyl acetate: petroleum ether = 1:15, vo...

Embodiment 3

[0023] Example 3: Preparation of 2-(3,5-diphenyl-4,5-dihydropyrazolyl)-N-methylaniline

[0024] At room temperature, add 0.30g (1mmol) 1-methyl-3-benzylbenzotriazole bromide, 0.10g (1mmol) styrene, 25mL tetrahydrofuran (THF) to a 50ml round bottom flask, stir for 10 Minutes later, 0.04 g (1 mmol) of sodium hydride (NaH) was added, followed by thin-layer chromatography (developing solvent: ethyl acetate:petroleum ether=1:5, volume ratio). After the reaction was completed, THF was concentrated under reduced pressure to recover THF, 10 ml of water and 20 ml of ethyl acetate were added to the residue, and the liquid was separated. Wash with saturated brine, and dry over anhydrous magnesium sulfate. Ethyl acetate was recovered by concentration under reduced pressure, and the residue was quickly separated by column chromatography (eluent: ethyl acetate: petroleum ether = 1:15, volume ratio) to obtain 0.16 g of a yellow solid product with a yield of 49.5%. Test data is with embodim...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a new method for preparing a 1,3,5-thriaryl substituted pyrazoline derivant. According to the method, the 1,3,5-thriaryl substituted pyrazoline derivant is prepared from 1,3-binary substituted benzotriazole salt, alkali and aryl-ethylene compound through a one-pot method. The method is mild in reaction conditions, fast in speed and good in selectivity, pyrazoline with a single structure is obtained, the product is easy to separate, and the method is simple to operate.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, in particular to a new method for preparing 1,3,5-triaryl-substituted pyrazoline derivatives. Background technique [0002] Pyrazoline and its derivatives are an important class of five-membered nitrogen heterocyclic compounds. The vast majority of pyrazoline compounds have a wide range of biological activities, such as antibacterial, antiviral, anticancer, sedative and analgesic, anti-inflammatory, etc., and are important pharmaceutical intermediates, such as: anti-arthritic drug Celebrex (J.Med Chem.1997,40,1347-1365), cannabinoid receptor antagonist rimonabant (Bioorg.Med.Chem.Lett.1996,6,1819-1824), etc. In addition, oxazoline compounds also have good optical properties, among which 1,3,5-triaryl substituted pyrazoline compounds have the most remarkable optical properties, and are widely used as photoluminescent materials, fluorescent anti-counterfeiting materials and decorative mat...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/06
Inventor 肖孝辉费祥文刘廷先洪丹燕
Owner ZHEJIANG NORMAL UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com