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

A kind of method for preparing pyrazole quinoxalinone derivative

A technology for pyrazole quinoxalinone and derivatives, which is applied in the field of preparation of pyrazole quinoxalinone derivatives, can solve the problems of high price, high toxicity, complex operation process, etc., and achieve rapid reaction, easy separation, and low raw material price cheap effect

Active Publication Date: 2020-06-26
浙江百斯特化工有限公司
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, quinoxaline compounds are mainly produced through 1,2-aryldiamine and 1,2-dicarbonyl compounds (such as: 1,2-diketone, 1,2-diester or oxalate, etc.) (TETRAHEDRON LETT .2001,42,4293-4295) by addition-condensation reaction, there are also reports of four-component one-pot synthesis of carboxylic acid, amine, isonitrile, aldehyde or ketone (ACS COMB.SCI.2014,16,403- 411), there are also literature reports on the use of noble metals as photocatalysts to prepare quinoxaline compounds (ADV.SYNTH.CATAL.2015,357,3696-3702), but the raw materials used in these methods are expensive and toxic Larger, complex operation process

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 kind of method for preparing pyrazole quinoxalinone derivative
  • A kind of method for preparing pyrazole quinoxalinone derivative
  • A kind of method for preparing pyrazole quinoxalinone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Preparation of 2-benzoyl-5-methylpyrazol[1,5-a]quinoxalin-4(5H)-one

[0023]

[0024] At room temperature, add 0.30g (1mmol) 1-methyl-3-(ethoxycarbonylmethylene) benzotriazole ylide bromide, 0.130g (1mmol) acetylenone to a 50-ml round-bottomed flask, 20 mL of acetonitrile (CH3CN), stirred for 10 minutes, added 0.11 g (1 mmol) of potassium tert-butoxide (t-BuOK), followed by thin-layer chromatography. After the reaction was over, CH CN was recovered by concentration under reduced pressure, 10 ml of water and 20 ml of ethyl acetate were added to the residue, the layers were separated, the organic phase was extracted with 2×20 ml of ethyl acetate, the organic layers were combined, and then 2×20 ml Washed with saturated brine and dried over anhydrous sodium sulfate. Ethyl acetate was recovered by concentration under reduced pressure, and the residue was quickly separated by column chromatography to obtain 0.212 g of a light yellow solid product with a yield of 70%. mp....

Embodiment 2

[0026] Preparation of 2-(4-chlorobenzoyl)-5-methylpyrazol[1,5-a]quinoxalin-4(5H)-one

[0027]

[0028] At room temperature, add 0.30g (1mmol) 1-methyl-3-(ethoxycarbonylmethylene) benzotriazole ylide bromide, 0.165g (1mmol) 1-( 4-Chlorophenyl) prop-2-yn-1-one, 20mL N,N-dimethylformamide (DMF), after stirring for 10 minutes, add 0.138g (1mmol) potassium carbonate (K2CO3), use TLC Chromatography trace. After the reaction, concentrate under reduced pressure to recover DMF, add 10 ml of water and 20 ml of ethyl acetate to the residue, separate the layers, extract the organic phase with 2 × 20 ml of ethyl acetate, combine the organic layers, and then use 2 × 20 ml Washed with saturated brine and dried over anhydrous sodium sulfate. Ethyl acetate was recovered by concentration under reduced pressure, and the residue was quickly separated by column chromatography to obtain 0.324 g of a light yellow solid product with a yield of 96%. mp.227-230℃; 1H NMR (600MHz, CDCl3) δ: 8.41 (d...

Embodiment 3

[0030] Preparation of 2-(4-fluorobenzoyl)-5-methylpyrazol[1,5-a]quinoxalin-4(5H)-one

[0031]

[0032]At room temperature, add 0.3g (1mmol) 1-methyl-3-(ethoxycarbonylmethylene) benzotriazole ylide bromide, 0.148g (1mmol) 1-( 4-Fluorophenyl) prop-2-yn-1-one, 20mL N,N-dimethylformamide (DMF), after stirring for 10 minutes, add 0.1382g (1mmol) potassium carbonate (K2CO3), use TLC Chromatography trace. After the reaction, concentrate under reduced pressure to recover DMF, add 10 ml of water and 20 ml of ethyl acetate to the residue, separate the layers, extract the organic phase with 2 × 20 ml of ethyl acetate, combine the organic layers, and then use 2 × 20 ml Washed with saturated brine and dried over anhydrous sodium sulfate. Ethyl acetate was recovered by concentration under reduced pressure, and the residue was quickly separated by column chromatography to obtain 0.315 g of a light yellow solid product with a yield of 98%. mp.140-143℃; 1H NMR (600MHz, CDCl3) δ: 8.49–8.4...

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 method for preparing a pyrazol quinoxaline ketone derivative. The method is characterized in that 1,3-disubstituded benzotriazole salt, alkaline and an unsaturated ketone compound are reacted by a one-pot method to prepare the pyrazol quinoxaline ketone derivative. The pyrazol quinoxaline ketone derivative has the following structure features shown in the attached figure,(The formula is shown in the description,.) wherein R1 is selected from hydrogen, alkyl, aryl or substituted aryl; R2 is selected from aryl or substituted aryl, and alkoxy. The method for preparing the pyrazol quinoxaline ketone derivative has the advantages that the operation is simple, the conditions are mild, the selectivity is good, the speed is quickhigh, and the product is easy to separate.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a method for preparing pyrazolequinoxalinone derivatives. Background technique [0002] Quinoxaline compounds are an important class of benzopyrazine nitrogen-heterocyclic compounds with extensive biological activities. They are many developed drugs (vitamin B2, panaplon, varenicline) and naturally active substances. (echinomycin) important skeleton. Quinoxaline compounds have good inhibitory effect on many pathogenic fungi (J Agric Food Chem.2014,62,9637-9643) and bacteria (Il Farmaco.2001,56,933-938), and have good anti- Allergic activity (J MedChem.1988,31,1098-1115), anticancer (Bioorg Med Chem.2008,16,6601-6610), anti-HIV-1 (AIDSRes Hum Retroviruses.2000,16,517-528), and quinoxa Phenyl compounds can also be used in photoelectric materials (Angew Chem Int Ed Engl. 2009, 48, 2474-2499), insecticide, weed control, anti-virus and other aspects. [0003] At present, quinoxalin...

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): C07D487/04
CPCC07D487/04
Inventor 肖孝辉鹿慧燕罗虹卢志勇
Owner 浙江百斯特化工有限公司
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