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Method for synthesizing quinoxaline compound under visible light induced iron catalysis condition

A visible light and quinoxaline technology, applied in organic chemistry and other fields, can solve difficult problems and achieve excellent efficiency and good selectivity

Active Publication Date: 2021-07-09
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the synthesis methods of quinoxaline compounds have been reported in a large number of literatures, but there are still some limitations in the direct synthesis of quinoxaline compounds from o-phenylenediamine: the reaction substrates need to be pre-functionalized in advance, for example, in the substrate Requires the presence of activating groups such as hydroxyl, carbonyl (e.g. o-diketones, o-diols, 2-aminoalcohols, and phenethylamines)
However, there is no literature report on the direct construction of quinoxaline compounds using non-activated aliphatic amines and o-phenylenediamine as substrates. It can be seen that visible light induces the coupling of non-activated aliphatic amines and o-phenylenediamines to form quinoxaline compounds. is very difficult

Method used

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  • Method for synthesizing quinoxaline compound under visible light induced iron catalysis condition
  • Method for synthesizing quinoxaline compound under visible light induced iron catalysis condition
  • Method for synthesizing quinoxaline compound under visible light induced iron catalysis condition

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Experimental program
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Effect test

Embodiment 1

[0036] Preparation of 2-methylquinoxaline

[0037] Get a quartz reaction tube, add a magnetic stirrer therein, then add 0.3mmol o-phenylenediamine, 0.6mmol tri-n-propylamine, 10mmol% photosensitizer iron salt (Fe 3 o 4 ), and finally 1 mL of dimethyl sulfoxide (DMSO) was added.

[0038] Then add a three-way gas guide head with a balloon above the quartz reaction tube, first use liquid nitrogen to freeze the reaction stock solution completely, then use an oil pump to evacuate the quartz reaction tube, and then fill the balloon with oxygen; stir with a magnetic stirrer Under the condition of oxygen, the reaction was carried out under the irradiation of xenon lamp (400-780nm) light for 48h, the final product was detected by TLC, and finally the final product 2-methylquinoxaline was obtained by separation by column chromatography with a yield of 73%. The reaction equation is as follows:

[0039]

[0040] The proton nuclear magnetic resonance spectrum characterization of 2-me...

Embodiment 2

[0043] Preparation of 2-Propylquinoxaline

[0044] Get a quartz reaction tube, add a magnetic stirrer therein, then add 0.3mmol o-phenylenediamine, 0.6mmol tripentylamine, 10mmol% photosensitizer iron salt (Fe(NO 3 ) 3 ), and finally 1 mL of dimethyl sulfoxide (DMSO) was added.

[0045] Then add a three-way gas guide head with a balloon above the quartz reaction tube, first use liquid nitrogen to freeze the reaction stock solution completely, then use an oil pump to evacuate the quartz reaction tube, and then fill the balloon with oxygen; stir with a magnetic stirrer Under oxygen conditions, the reaction was performed under blue LED light for 48 hours, the final product was detected by TLC, and finally the final product 2-propylquinoxaline was obtained by separation by column chromatography with a yield of 70%. The reaction equation is as follows:

[0046]

[0047] 2-Propylquinoxaline H NMR spectrum is characterized as follows: 8.65 (s, 1H), 8.05-7.84 (m, 2H), 7.70-7.54 ...

Embodiment 3

[0049] Preparation of 2-butyl-6,7-dihydroquinoxaline

[0050] Get a quartz reaction tube, add a magnetic stirrer thereto, then add 0.3mmol o-phenylenediamine, 0.6mmol trihexylamine, 10mmol% photosensitizer iron salt (FeSO 4 ), and finally 1 mL of dimethyl sulfoxide (DMSO) was added.

[0051] Then add a three-way gas guide head with a balloon above the quartz reaction tube, first use liquid nitrogen to freeze the reaction stock solution completely, then use an oil pump to evacuate the quartz reaction tube, and then fill the balloon with oxygen; stir with a magnetic stirrer Under the condition of oxygen, it was reacted for 48h under the irradiation of xenon lamp (400-780nm) light, the final product was detected by TLC, and finally the final product 2-butyl-6,7-dihydroquinoxaline was obtained by column chromatography separation, producing The rate is 77%. The reaction equation is as follows:

[0052]

[0053] The proton nuclear magnetic resonance spectrum of 2-butyl-6,7-dih...

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Abstract

The invention belongs to the technical field of compound synthesis, and particularly relates to a method for synthesizing quinoxaline compounds under visible light induced iron catalysis conditions. The method comprises the following steps: by taking non-activated aliphatic amine and o-phenylenediamine as raw materials, under the action of a photosensitizer, under the illumination of visible light, reacting in a solvent at room temperature and under oxygen conditions to generate the quinoxaline compound. The method has better substrate universality and relatively mild reaction conditions, not only realizes synthesis of the quinoxaline compound for the first time, but also widens the field of organic synthesis.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and in particular relates to a method for synthesizing quinoxaline compounds under the condition of iron catalysis induced by visible light. Background technique [0002] As an important class of nitrogen-containing heterocyclic compounds, quinoxaline compounds are widely used in the synthesis of chemistry, medicine, pesticides and materials science. At present, the synthesis methods of quinoxaline compounds have been reported in a large number of literatures, but there are still some limitations in the direct synthesis of quinoxaline compounds from o-phenylenediamine: the reaction substrates need to be pre-functionalized in advance, for example, in the substrate The presence of activating groups such as hydroxyl, carbonyl (eg o-diketones, o-diols, 2-aminoalcohols and phenethylamines) is required. However, the method of directly synthesizing quinoxaline compounds from non-activated al...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/42C07D241/38
CPCC07D241/42C07D241/38
Inventor 徐元清史作冬许静徐浩张文凯刘保英李建通王延鹏任艳蓉丁涛房晓敏
Owner HENAN UNIVERSITY
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