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Azo compound and synthesis method and application thereof

A technology of azo compounds and synthetic methods, applied in the direction of organic chemistry, etc., can solve the problems of precious reaction catalysts and the need to prepare substrates

Active Publication Date: 2021-05-18
ANQING NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0031] It can be seen that the N=N double bond of the azo compound constructed by the above reaction is directly connected to the benzene ring, and some reaction catalysts are expensive, and the substrate needs to be prepared

Method used

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  • Azo compound and synthesis method and application thereof
  • Azo compound and synthesis method and application thereof
  • Azo compound and synthesis method and application thereof

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Experimental program
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preparation example Construction

[0072] The invention provides a kind of synthetic method of azo compound, comprises the following steps:

[0073] reacting substrate a and substrate b in a solvent to obtain the azo compound;

[0074] The structural formula of the substrate a is:

[0075] Among them, R 1 ~R 5 is independently one of hydrogen, hydroxy and methoxy;

[0076] The substrate b is selected from the following compounds:

[0077]

[0078] In the present invention, substrate a is preferably:

[0079] One of.

[0080] In the present invention, the substrate b is preferably:

[0081] One of.

[0082] In the present invention, the substance amount ratio of the substrate a and the substrate b is 1-3:0.5-1.5, preferably 2:1.

[0083] In the present invention, the reaction temperature is 80-180°C, preferably 90°C, and the reaction time is 1.5-2.5h, preferably 2h.

[0084] In the present invention, the solvent is one or more of dimethylacetamide, triethylamine, dimethyl sulfoxide and water,...

Embodiment 1

[0090] Put 0.2 mmol of substrate 1-a, 0.1 mmol of substrate 1-b, and 5 mg of ferrous chloride catalyst into water for reaction. The reaction temperature was controlled at 90° C. After 2 hours, the reaction was completed to obtain compound 1.

[0091] Wherein the structural formula of substrate 1-a is: The structural formula of substrate 1-b is The structural formula of compound 1 is The yield was 81%.

Embodiment 2

[0093] Put 0.2 mmol of substrate 2-a, 0.05 mmol of substrate 2-b, and 7.5 mg of ferrous chloride catalyst into water for reaction, the reaction temperature was controlled at 90°C, and the reaction was completed after 2 hours to obtain compound 2.

[0094] Wherein the structural formula of substrate 2-a is: The structural formula of substrate 2-b is The structural formula of compound 2 is The yield was 82.5%.

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Abstract

The invention relates to the technical field of organic synthesis, in particular to an azo compound-N = N (nitrogen-nitrogen double bond) and a synthesis method and application thereof. The N = N double-bond compound is prepared through a simple one-pot synthesis method based on acetophenone derivatives and 1, 3-diaminoguanidine hydrochloride (and hydrazine compounds) as substrates, nitrogen-nitrogen double bonds of the azo compound prepared through the method are connected to aliphatic carbon, and the method is simple in raw material, mild in reaction condition, green and environment-friendly in reaction system, and the azo compound obtained by the method can be applied to the fields of dyes, optical materials and the like.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to an azo compound and its synthesis method and application. Background technique [0002] There are not many reports on the synthesis of nitrogen-nitrogen double bonds based on different substrates. According to the current literature summary, there are the following methods: [0003] (1) Diazotization reaction [0004] Based on diazonium salts and o-methoxyphenol substrates, Hagh-been K et al. 2 CO 3 Solution system reaction to synthesize aromatic azobenzene. Because the nitro group on the diazonium salt is an electron-withdrawing group, the reaction is easy to carry out. [0005] [0006] Haghbeen K, Tan E W. Synthesis of catechol azo dyes [J]. The Journal of Organic Chemistry, 1998, 63(19): 4503-4505. [0007] (2) Mills reaction [0008] Herges R reduced aromatic nitro compounds to corresponding nitroso compounds under alkaline conditions, using zinc powder as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/04
CPCC07C245/04
Inventor 庞韬章超
Owner ANQING NORMAL UNIV
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