Method for synthesizing cinchona alkaloids microwave radiation non-solvent

A technology of cinchona alkaloids and a synthesis method is applied in the field of solvent-free synthesis of cinchona alkaloid derivatives by microwave irradiation, and the effects of increasing power, mild reaction conditions and prolonging reaction time are achieved.

Inactive Publication Date: 2008-08-20
FOURTH MILITARY MEDICAL UNIVERSITY
View PDF1 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chinese invention patent (ZL200510043141.2) discloses a new acid-binding agent ...

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
  • Method for synthesizing cinchona alkaloids microwave radiation non-solvent
  • Method for synthesizing cinchona alkaloids microwave radiation non-solvent
  • Method for synthesizing cinchona alkaloids microwave radiation non-solvent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: the synthesis of derivative 1:

[0027] In the 50mL round bottom flask, add 0.295g (0.0015mol) 1,4-dichloro-2,3 naphthyridine, 0.487g (0.0015mol) quinine, 0.84g (0.006mol) K 2 CO 3 , a catalytic amount of tetrabutylammonium bromide (TBAB), magnetically stirred and mixed evenly, placed in a microwave reactor, adjusted power 850W, temperature 125°C, reacted for 10min, monitored by TLC, added CH 2 Cl 2 After extraction (25 mL×3), the organic layers were combined, concentrated under reduced pressure, and separated by column chromatography to obtain 0.58 g of a light yellow solid with a yield of 68.7%.

Embodiment 2

[0028] Embodiment 2: the synthesis of derivative 2:

[0029] In the 50mL round bottom flask, add 0.295g (0.0015mol) 1,4-dichloro-2,3 naphthyridine, 0.97g (0.003mol) quinine, 1.7g (0.012mol) K 2 CO 3 , a catalytic amount of tetrabutylammonium chloride, magnetically stirred and mixed evenly, placed in a microwave reactor, adjusted power 850W, temperature 135°C, reacted for 5min, monitored by TLC, added CH after the reaction was completed 2 Cl 2 Extract (25mL×3), combine the organic layers, concentrate under reduced pressure, and separate by flash column chromatography, the yield is 73.8%.

Embodiment 3

[0030] Embodiment 3: the synthesis of derivative 3:

[0031] In the 50mL round bottom flask, add 1.77g (0.006mol) cinchonine, 1.19g (0.006mol) 1,4-dichloro-2,3 naphthyridine, 3.38g (0.024mol) K 2 CO 3 , a catalytic amount of tetrabutylammonium bromide (TBAB), magnetically stirred and mixed evenly, placed in a microwave reactor, adjusted power 800W, temperature 120°C, reacted for 10min, monitored by TLC, added CH 2 Cl 2 After extraction (75mL×3), the combined organic layers were concentrated under reduced pressure and separated by flash column chromatography with a yield of 75.8%.

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 of the solvent-free synthesis of cinchona alkaloid derivatives by adopting microwave radiation with the catalysis of a phase transfer catalyst. According to the method of the invention, 1, 4-dichloro-2, 3-naphthyridine, 3, 6-dichloropyridazine, 4, 6-dichloropyrimidines, 2, 5-diphenyl-4, 6-dichloropyrimidines or phthalic acid can react with quinine, hydroquinine, quinidine, dihydro quinidine, cinchonine or cinchonidine according to a mol ratio of 1:3 to 3:1 to obtain the cinchona alkaloid derivatives. Under the action of microwave, the synthetic process of the cinchona alkaloid derivatives can become simple and safe in operation, short in reaction time, and mild in reaction condition; more particularly, toxic organic solvents such as methylbenzene and DMF with a high boiling point, etc. are not adopted in the course of the reaction, thus being in line with the megatrend of green chemistry, furthermore, monosubstituted products and disubstituted products can be obtained with high yield by the control of reaction time and power.

Description

technical field [0001] The invention relates to a method for synthesizing cinchona alkaloid derivatives under microwave radiation catalyzed by a phase transfer catalyst. These cinchona alkaloid derivatives can be widely used in various asymmetric catalytic reactions. Background technique [0002] Chirality is one of the characteristics of nature and the basis of all life. Life phenomena depend on the existence and recognition of chirality. All animals, plants and the human body have precise chiral recognition capabilities for drugs. The configurations of chiral drugs are different, and their physiological activities and toxicity are also different. L-dopa is a good medicine for treating Parkinson's disease, but D-dopa has serious side effects. (S)-naproxen is 35 times more potent than the (R)-isomer. Therefore, how to obtain chiral compounds has become a severe challenge for chemists. Although optically pure compounds can be obtained through classic racemate resolution a...

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
IPC IPC(8): C07D453/04B01J31/02
Inventor 孙晓莉王平安王海波景临林张生勇
Owner FOURTH MILITARY MEDICAL UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap