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A kind of preparation method of 2-aryl substituted quinoline nitrogen oxide compound

A technology for quinoline nitrogen oxides and oxygen compounds, which is applied in the field of preparation of 2-arylquinoline nitrogen oxide derivatives, can solve problems such as poor regioselectivity, expensive reaction conditions, etc. The effect of mass production

Active Publication Date: 2022-03-04
HARBIN INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The present invention aims to solve the problem that the existing direct functionalization method of quinoline nitrogen oxides uses harsh reaction conditions such as expensive transition metal catalysts, high temperature, etc., uses flammable and explosive diazo organic compounds as raw materials, and has poor regioselectivity and other technical problems, and provide a kind of preparation method of 2-aryl substituted quinoline nitrogen oxide compound

Method used

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  • A kind of preparation method of 2-aryl substituted quinoline nitrogen oxide compound
  • A kind of preparation method of 2-aryl substituted quinoline nitrogen oxide compound
  • A kind of preparation method of 2-aryl substituted quinoline nitrogen oxide compound

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Embodiment 1

[0035] Embodiment 1: The preparation method of the 2-phenyl substituted quinoline nitrogen oxide compound of the present embodiment is carried out according to the following steps:

[0036] One, at room temperature, with 73.6mg (0.2mmol) diphenyl iodine tetrafluoroborate, 14.5mg (0.1mmol) quinoline nitrogen oxide, 7.1mg (10mol%) eosin Y photocatalyst, 32.5mg (0.1 mmol) cesium carbonate and 21.6mg (0.2mmol) benzoquinone were added to a 10mL penicillin bottle, sealed with a rubber stopper and a parafilm; use a needle to connect the reaction system and an air pump, extract the air in the reaction system, backfill with nitrogen, repeat three times , form a nitrogen atmosphere in the penicillin bottle, then inject 1mL of methanol, and mix well; light the penicillin bottle with 5W blue LEDs light for reaction, monitor the reaction progress with TLC, and the reaction is completed in 3 days;

[0037] Two, after the reaction finishes, the rotary evaporator rotates and evaporates and re...

Embodiment 2

[0045] Embodiment 2: The preparation method of the 3-methyl-2-phenyl substituted quinoline nitrogen oxide compound of the present embodiment is carried out according to the following steps:

[0046] 1. At room temperature, 73.6mg (0.2mmol) diphenyl iodine tetrafluoroborate, 15.9mg (0.1mmol) 3-methylquinoline nitrogen oxide, 7.1mg (10mol%) eosin Y photocatalyst, 32.5 Add mg (0.1mmol) cesium carbonate and 21.6mg (0.2mmol) benzoquinone to a 10mL penicillin bottle, seal it with a rubber stopper and a parafilm; use a needle to connect the reaction system and an air pump, pump out the air in the reaction system, and backfill it with nitrogen , repeat three times, form a nitrogen atmosphere in the penicillin bottle, then inject 1mL methanol, mix well; light the penicillin bottle with 9W blue LEDs light to react, monitor the progress of the reaction with TLC, and the reaction is completed after 3 days;

[0047] Two, after the reaction is finished, the rotary evaporator is used to remo...

Embodiment 3

[0056] Embodiment 3: The preparation method of the 3-chloro-2-phenyl substituted quinoline nitrogen oxide compound of the present embodiment is carried out according to the following steps:

[0057] One, at room temperature, with 73.6mg (0.2mmol) diphenyl iodine tetrafluoroborate, 18.0mg (0.1mmol) 3-chloroquinoline nitroxide, 7.1mg (10mol%) eosin Y photocatalyst, 32.5mg ( Add 0.1mmol) cesium carbonate and 21.6mg (0.2mmol) benzoquinone to a 10mL penicillin bottle, seal it with a rubber stopper and a parafilm; use a needle to connect the reaction system and an air pump, pump out the air in the reaction system, backfill with nitrogen, repeat Three times, form a nitrogen atmosphere in the penicillin bottle, then inject 1mL of methanol, mix well; light the penicillin bottle with 10W blue LEDs light to react, monitor the reaction progress with TLC, and the reaction is completed in 3 days;

[0058] Two, after the end of the reaction, the rotary evaporator is rotary evaporated to remo...

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Abstract

A kind of preparation method of 2-aryl substituted quinoline nitrogen oxide compound, it relates to the preparation method of 2-aryl quinoline nitrogen oxide derivative, it is to solve the direct functionalization method of existing quinoline nitrogen oxide The technical problems of expensive transition metals, harsh preparation conditions, flammable and explosive raw materials, and poor regioselectivity of products. This method: add diaryliodonium tetrafluoroborate, quinoline nitrogen oxide, eosin Y catalyst, alkali and additives into a transparent reactor at room temperature, seal it; inject an organic solvent under a nitrogen atmosphere, and mix evenly; Use blue LEDs light to react; spin to remove the solvent, and then separate and purify to obtain 2-aryl substituted quinoline nitrogen oxide compound; the structural formula of the 2-aryl substituted quinoline nitrogen oxide compound is: it can be used as a drug lead compound Screening or for biological activity testing, research use. It can also be used to synthesize other 2-arylquinoline nitrogen-oxygen derivatives.

Description

technical field [0001] The invention relates to a preparation method of 2-arylquinoline nitrogen oxide derivatives, belonging to the field of organic synthesis. Background technique [0002] Quinoline oxynitride is an important organic alkaloid, and the bi-arene compound skeleton with quinoline oxynitride widely exists in natural products, drugs, organic compounds with biological activity, ligands and organic functional materials. For example, compounds (compound 1) with anti-cancer, anti-inflammatory and therapeutic effects on diabetes, anti-inflammatory and anti-fibrosis compounds (compound 2), anti-cancer and anti-inflammatory compounds (compound 3) all have the skeleton of 2-aryl quinoline nitrogen oxide structure. Therefore, many chemists are devoted to the synthesis and modification of quinoline nitrogen oxides and their derivatives. The traditional synthesis of quinoline oxynitride-arene compounds often requires the use of classical coupling reactions, such as Still...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/60
CPCC07D215/60
Inventor 姜再兴高国林李大志
Owner HARBIN INST OF TECH