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Preparation method of 2,3,4-trisubstituted quinoline-N-oxide compound

A technology for quinoline nitroxides and compounds, which is applied in the field of preparation of quinoline nitroxides and achieves the effect of wide source of raw materials

Active Publication Date: 2017-03-08
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on the synthesis of quinoline nitrogen oxides by other methods.

Method used

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  • Preparation method of 2,3,4-trisubstituted quinoline-N-oxide compound
  • Preparation method of 2,3,4-trisubstituted quinoline-N-oxide compound
  • Preparation method of 2,3,4-trisubstituted quinoline-N-oxide compound

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Embodiment Construction

[0030] The present invention will be further described below in conjunction with specific embodiments.

[0031] Add nitrone (II) (0.3mmol), alkyne (III) (0.2mmol), catalyst Cp * Co(CO)I 2 (0.02mmol), silver tetrafluoroborate (0.04mmol), silver acetate (0.4mmol) and 2ml of organic solvent, mixed and stirred evenly, after completing the reaction according to the reaction conditions in Table 2, washed, dried, mixed with silica gel, passed through the column layer Analyze and purify to obtain corresponding quinoline nitrogen oxide compound (I), the reaction process is shown in the following formula:

[0032]

[0033] Table 1

[0034]

[0035] Table 2

[0036]

[0037] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, Me is methyl, DCP is 2,6-dichlorophenyl, Cp * is pentamethylcyclopentadienyl, Ph is phenyl.

[0038] In the present invention, the preparation method of raw materials can refer to: Wang, C.X.; Wang, D.; Yan, H.; Wang, H.; Pan...

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Abstract

The invention discloses a preparation method of a 2,3,4-trisubstituted quinoline-N-oxide compound. The method comprises the following steps that under the effect of a cobalt catalyst, an additive and an oxidizing agent, a nitrone compound and an alkyne compound produce ring reaction in an organic solvent; after the reaction is completed, post treatment is performed to obtain the quinoline-N-oxide compound. The preparation method has the advantages that the use raw materials have wide resources; the method can be used for synthesizing the quinoline-N-oxide compound with various substitutional groups; important application values are realized.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of 2,3,4-trisubstituted quinoline nitrogen-oxygen compounds. Background technique [0002] As an important quinoline derivative, quinoline nitrogen-oxygen compounds have very different properties from the unoxidized parent compound, showing significantly different chemical reactivity. It has been widely used in medicine, catalysis and other fields. For example, quinoline nitrogen oxides substituted with 6-position α, β-unsaturated ketones have obvious antifungal activity, and biquinoline nitrogen oxides are an excellent hand. Catalysts can efficiently realize the reduction of aldehydes, ketones and alkenes. At the same time, it can also be used as a metal chelating agent to effectively coordinate with various metals, and it is also widely used in the field of analytical chemistry. The 4-alkene substituted quinoline nitrogen oxides are important ...

Claims

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Application Information

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IPC IPC(8): C07D215/60
CPCC07D215/60
Inventor 张玉红刘岳王晨吕宁宁刘占祥
Owner ZHEJIANG UNIV
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