Method for catalytically synthesizing phenazine compounds in water phase under microwave radiation

A technology of microwave irradiation and aqueous phase, applied in the direction of organic chemistry, can solve the problems of difficulty in obtaining raw materials, severe reaction conditions, and high toxicity of reagents, and achieve the effects of environmental friendliness, simple operation and low cost.

Active Publication Date: 2015-11-25
FUJIAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 ...

Method used

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  • Method for catalytically synthesizing phenazine compounds in water phase under microwave radiation
  • Method for catalytically synthesizing phenazine compounds in water phase under microwave radiation
  • Method for catalytically synthesizing phenazine compounds in water phase under microwave radiation

Examples

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Effect test

Embodiment 1

[0042] Example 1: Phenazine: Add 1mmol of 2-iodoaniline to the reaction vessel, add 0.1mmol of iron chloride, 0.1mmol of lithium proline (prolinelithiumas), 3mmol of sodium hydroxide, and 4-butylammonium bromide (( n Bu) 4 NBr) 0.1mmol, water 3mL. Placed in a microwave reactor and heated to 100°C under 150W power for continuous reaction for 30min. After the reaction, it was cooled to room temperature and concentrated under reduced pressure. 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: Add 1mmol of 2-iodo-4-methylaniline to the reaction vessel, add 0.1mmol of ferric chloride, 0.1mmol of lithium proline (prolinelithiumas), 3mmol of sodium hydroxide, and 4-butylammonium bromide (( n Bu) 4 NBr) 0.1mmol, water 3mL. Placed in a microwave reactor and heated to 100°C under 150W power for continuous reaction for 30min. After the reaction, it was cooled to room temperature and concentrated under reduced pressure. 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%.

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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

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Application Information

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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
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