A method for catalytically synthesizing phenazine compounds under microwave irradiation in aqueous phase

A technology of microwave radiation and water phase, which is applied in the field of preparation of phenazine derivatives, can solve the problems of severe reaction conditions, difficulty in obtaining raw materials, and high toxicity of reagents, and achieves the effects of simple operation, environmental friendliness, and low cost

Active Publication Date: 2017-08-25
FUJIAN MEDICAL UNIV
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis methods of phenazine compounds currently reported have their own advantages and disadvantages, and their use is more or less limited due to the difficulty in obtaining raw materials, the high toxicity of some reagents, the severe reaction conditions and serious environmental pollution.

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 catalytically synthesizing phenazine compounds under microwave irradiation in aqueous phase
  • A method for catalytically synthesizing phenazine compounds under microwave irradiation in aqueous phase
  • A method for catalytically synthesizing phenazine compounds under microwave irradiation in aqueous phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: Phenazine: 1 mmol of 2-iodoaniline was added to the reaction vessel, followed by adding 0.1 mmol of ferric chloride, 0.1 mmol of lithium proline (proline lithiumas), 3 mmol of sodium hydroxide, 4-butyl bromide Ammonium (( n Bu) 4 NBr) 0.1 mmol, water 3 mL. Placed in a microwave reactor and heated to 100 °C under 150 W power for continuous reaction for 30 min. After the reaction was completed, it was cooled to room temperature, concentrated under reduced pressure, and the product was purified by column chromatography to obtain a yellow solid with a yield of 79%.

Embodiment 2

[0043] Example 2: 2,7-dimethylphenazine: 1 mmol of 2-iodo-4-methylaniline was added to the reaction vessel, followed by adding 0.1 mmol of ferric chloride and 0.1 mmol of lithium proline (proline lithiumas), Sodium hydroxide 3 mmol, 4-butylammonium bromide (( n Bu) 4 NBr) 0.1 mmol, water 3 mL. Placed in a microwave reactor and heated to 100 °C under 150 W power for 30 min. After the reaction was completed, it was cooled to room temperature, concentrated under reduced pressure, and the product was purified by column chromatography to obtain a yellow solid with a yield of 84%.

Embodiment 3

[0044] Example 3: 2,7-diethylphenazine: The preparation method is the same as in Example 2, adding 1 mmol of 2-iodo-4-ethylaniline to obtain a yellow solid with a yield of 86%.

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 catalytically synthesizing phenazine compounds in a water phase under microwave radiation, which comprises the following steps: adding a catalytic amount of catalyst ferric chloride or nickelous chloride, a cocatalyst lithium proline, a substrate substituted 2-haloaniline, a phase-transfer catalyst 4-butyl ammonium chloride, 4-butyl ammonium bisulfate or 4-butyl ammonium bromide, an inorganic alkali or organic alkali and water into a reaction vessel, putting into a microwave reaction instrument, reacting at certain temperature under certain power for some time, concentrating under reduced pressure, and purifying the product by column chromatography. The method for preparing phenazine compounds is friendly to the environment, simple to operate and high in efficiency. Compared with the prior art, the method has the advantages of obviously higher reaction speed than conventional heating, mild reaction conditions, high yield, high safety, low cost and environment friendliness, and is simple to operate.

Description

technical field [0001] The present invention relates to a method for the preparation of phenazine derivatives. That is, using substituted 2-halogenated arylamines as raw materials, introducing microwaves as an auxiliary synthesis method, and efficiently catalyzing and rapidly preparing phenazine compounds. Background technique [0002] As a class of nitrogen-containing fused heterocyclic compounds, phenazine has a certain special status in the field of organic chemistry. It is a dyeable substance obtained by chemical methods for the first time. Later, it was discovered that phenazine was biologically active and could be used as a fungicide. In recent years, phenazine has been used more and more widely, such as in antitumor drugs, antibacterial, molecular optical switches, solar energy conversion and polymer materials, and has attracted more and more attention in the fields of medicine, energy and materials. [0003] The methods for synthesizing phenazine compounds reported...

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): C07D241/46
CPCC07D241/46
Inventor 柯方林巧发许建华刘洋林晨李鹏
Owner FUJIAN MEDICAL UNIV
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