Preparation method of 2-phenyl substituted pyridine nitrogen oxide compound

A technology for pyridine nitrogen oxide compounds and pyridine nitrogen oxide derivatives, which is applied in the field of preparation of pyridine nitrogen oxide derivatives, can solve the problems of harsh reaction conditions, poor regioselectivity, flammable catalysts and the like, and achieves simple operation, potential biological activity, The effect of catalyst safety

Active Publication Date: 2020-02-28
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 technical problems of flammability, explosion, harsh reaction conditions and poor regioselectivity ...

Method used

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  • Preparation method of 2-phenyl substituted pyridine nitrogen oxide compound
  • Preparation method of 2-phenyl substituted pyridine nitrogen oxide compound
  • Preparation method of 2-phenyl substituted pyridine nitrogen oxide compound

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Experimental program
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Embodiment 1

[0029] Embodiment 1: The preparation method of the 2-phenyl substituted pyridine nitrogen oxide compound of the present embodiment 1 is carried out according to the following steps:

[0030] 1. At room temperature, mix 9.5mg (0.1mmol) pyridine nitrogen oxide, 73.6mg (0.2mmol) diphenyl iodine tetrafluoroborate, 7.1mg (10mol%) eosin Y photocatalyst, 32.5mg (0.1mmol) Cesium carbonate and 54.1 mg (0.2 mmol) K 2 S 2 o 8 Add it into a 10mL penicillin bottle, seal it with a rubber stopper and a parafilm; then use a needle to connect the penicillin bottle to an air pump, pump out the air in the penicillin bottle, backfill it with nitrogen, repeat three times, a nitrogen atmosphere is formed in the penicillin bottle, and then inject 1mL of methanol As a solvent, mix well; at room temperature, the reactor is illuminated with 5W blue LEDs for reaction, and the reaction progress is monitored by TLC, and the reaction is completed after 3 days;

[0031] Two, after the reaction finishes, ...

Embodiment 2

[0039] Embodiment 2: The preparation method of the 2-phenyl substituted pyridine nitrogen oxide compound of this embodiment is carried out according to the following steps:

[0040] 1. At room temperature, mix 14.0mg (0.1mmol) 4-nitropyridine nitroxide, 73.6mg (0.2mmol) diphenyl iodine tetrafluoroborate, 7.1mg (10mol%) eosin Y photocatalyst, 32.5mg (0.1mmol) cesium carbonate and 54.1mg (0.2mmol) K 2 S 2 o 8 Add it into a 10mL penicillin bottle, seal it with a rubber stopper and a parafilm; then use a needle to connect the penicillin bottle to an air pump, pump out the air in the penicillin bottle, backfill it with nitrogen, repeat three times, a nitrogen atmosphere is formed in the penicillin bottle, and then inject 1mL of methanol As a solvent, mix well; at room temperature, the reactor is illuminated with 10W blue LEDs light for reaction, and the reaction progress is monitored by TLC, and the reaction is completed after 2 days of reaction;

[0041]Two, after the reaction ...

Embodiment 3

[0050] Embodiment 3: The preparation method of the 2-phenyl substituted pyridine nitrogen oxide compound of this embodiment is carried out according to the following steps:

[0051] 1. At room temperature, 12.0mg (0.1mmol) of 4-cyanopyridine nitroxide, 73.6mg (0.2mmol) of diphenyl iodine tetrafluoroborate, 7.1mg (10mol%) of eosin Y photocatalyst, 32.5mg (0.1mmol) cesium carbonate and 54.1mg (0.2mmol) K 2 S 2 o 8 Add it into a 10mL penicillin bottle, seal it with a rubber stopper and a parafilm; then use a needle to connect the penicillin bottle to an air pump, pump out the air in the penicillin bottle, backfill it with nitrogen, repeat three times, a nitrogen atmosphere is formed in the penicillin bottle, and then inject 1mL of methanol As a solvent, mix well; at room temperature, the reactor is illuminated with 15W blue LEDs light for reaction, and the reaction progress is monitored by TLC, and the reaction is completed after 2 days of reaction;

[0052] Two, after the rea...

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Abstract

The invention discloses a preparation method of a 2-phenyl substituted pyridine nitrogen oxide compound, relates to a preparation method of a pyridine nitrogen oxide derivative, and aims to solve thetechnical problems of flammability, explosiveness, harsh reaction conditions and poorer regioselectivity of a catalyst in the conventional direct selective functionalization method. The method comprises the following steps: adding the pyridine nitrogen oxide derivative, diphenyl iodide tetrafluoroborate, an eosin Y catalyst, an alkali and an additive into a transparent reactor at room temperature,and sealing; replacing air in the reactor with nitrogen to form a nitrogen atmosphere, injecting a solvent, and uniformly mixing; irradiating the reactor with blue LEDs lamp light for reaction; afterthe reaction is finished, removing the solvent through rotary evaporation, and then performing separation and purification of prefabricated silica gel column chromatography to obtain the 2-phenyl substituted pyridine nitrogen oxide compound, and the structural formula of the 2-phenyl substituted pyridine nitrogen oxide compound is as shown in the specification, R1 is hydrogen, alkyl, nitrile group, halogen, phenyl or nitro; the 2-phenyl substituted pyridine nitrogen oxide compound can be used in the fields of screening of drug lead compounds or biological activity test and research.

Description

technical field [0001] The invention relates to a preparation method of pyridine nitrogen oxide derivatives, belonging to the field of organic synthesis. Background technique [0002] Pyridine nitrogen oxide is an important organic alkaloid. The 2-phenylpyridine nitrogen oxide skeleton with pyridine nitrogen oxide widely exists in natural products, organic compounds with biological activity, drugs, ligands and organic functional materials. For example, compounds with anti-infective effects (compound 1), anti-cancer compounds (compound 2), anti-inflammatory, anti-anemia, anticoagulant, respiratory system, anti-angina pectoris, cardiovascular drug compounds (compound 3) all have 2-phenyl Skeleton structure of pyridine nitrogen oxide. Therefore, in the past few decades, many chemists around the world have devoted themselves to the synthesis and modification of pyridine nitrogen oxides and their derivatives. The traditional synthesis of 2-phenylpyridine nitroxide often require...

Claims

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Application Information

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IPC IPC(8): C07D213/89
CPCC07D213/89
Inventor 姜再兴高国林李大志
Owner HARBIN INST OF TECH
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