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1, 2, 4-triazole compound and preparation method thereof

A technology of hydrazine compounds and compounds, applied in the field of organic intermediates, can solve problems such as danger and explosive raw materials

Inactive Publication Date: 2020-08-11
GANNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, most of the methods for constructing 1,2,4-triazole compounds use azide as raw material at room temperature, and the raw material is explosive and dangerous

Method used

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  • 1, 2, 4-triazole compound and preparation method thereof
  • 1, 2, 4-triazole compound and preparation method thereof
  • 1, 2, 4-triazole compound and preparation method thereof

Examples

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preparation example Construction

[0055] The present invention provides a preparation method of 1,2,4-triazole compounds described in the above scheme, comprising the following steps:

[0056] Mix hydrazine compounds, isothiocyanate compounds, tetramethylguanidine, photocatalysts and polar organic solvents to obtain a mixed solution; the mixed solution undergoes a cyclization reaction under light and a temperature of 50-80°C, Obtain the 1,2,4-triazole compound;

[0057] The structural formula of the hydrazine compound is R 1 -NHNH 2 ; The structural formula of the isothiocyanate compound is R 2 N=C=S; the photocatalyst is an organic dye and / or a metal complex.

[0058] The invention mixes hydrazine compound, isothiocyanate compound, tetramethylguanidine, photocatalyst and polar organic solvent to obtain mixed solution. In the present invention, the structural formula of the hydrazine compound is R 1 -NHNH 2 , R in the structural formula of hydrazine compounds 1 and R in the structure shown in formula I ...

Embodiment 1

[0069] A 1,2,4-triazole compound having a structure shown in formula I-(1):

[0070]

[0071] Preparation method: add 0.1mmol phenylhydrazine, 0.1mmol phenyl isothiocyanate, 0.15mmol tetramethylguanidine, and 1L acetonitrile to the reaction tube and mix, then add 0.001mmol rose bengal to it, and place the resulting mixture at 465nm Under the irradiation of light source, the reaction was stirred at 60°C for 24 hours. After the reaction, it was separated and purified by column chromatography. The volume ratio of petroleum ether and ethyl acetate in the column chromatography eluent was 5:1, and the purified target product was obtained. Yield 70%, purity 99.9%.

[0072] The structure of the obtained product is characterized, and the proton nuclear magnetic resonance spectrum and the carbon nuclear magnetic resonance spectrum are respectively as follows figure 1 with figure 2 As shown, the structural characterization data are as follows:

[0073] 1 HNMR (400MHz, CDCl 3 ,pp...

Embodiment 2

[0078] A 1,2,4-triazole compound having a structure shown in formula I-(2):

[0079]

[0080] Preparation method: Add 0.1mmol 4-chlorophenylhydrazine, 0.1mmol phenyl isothiocyanate, 0.15mmol tetramethylguanidine, and 1mL acetonitrile into a reaction tube and mix them, then add 0.001mmol Rose Bengal, and mix the resulting mixture Placed under the irradiation of a 465nm light source, stirred and reacted at 60°C for 12 hours, separated and purified by column chromatography after the reaction, the volume ratio of petroleum ether and ethyl acetate in the column chromatography eluent was 5:1, and the purified target was obtained The product has a yield of 34% and a purity of 99.9%.

[0081] The structure of the obtained product is characterized, and the proton nuclear magnetic resonance spectrum and the carbon nuclear magnetic resonance spectrum are respectively as follows image 3 with Figure 4 As shown, the structural characterization data are as follows:

[0082] 1 HNMR (...

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Abstract

The invention provides a 1, 2, 4-triazole compound and a preparation method thereof, and relates to the technical field of organic intermediates. The 1, 2, 4-triazole compound provided by the invention has a structure as shown in a formula I, is a 1, 2, 4-triazole compound with a novel structure, expands the variety of the 1, 2, 4-triazole compound, and can be applied to pharmaceutical chemistry.The invention also provides a preparation method of the 1, 2, 4-triazole compound, which comprises the following steps: mixing a hydrazine compound, an isothiocyanate compound, tetramethylguanidine, aphotocatalyst and a polar organic solvent, and carrying out cyclization reaction on an obtained mixed solution under the conditions of illumination and temperature of 50-80 DEG C to obtain the 1, 2,4-triazole compound. The 1, 2, 4-triazole compound can be obtained at the temperature of 50-80 DEG C by providing energy required by reaction through illumination, the reaction process is safe and stable, conditions are mild, operation is convenient, and control is easy.

Description

technical field [0001] The invention relates to the technical field of organic intermediates, in particular to a 1,2,4-triazole compound and a preparation method thereof. Background technique [0002] Chemists are very interested in the synthesis of triazole compounds, which have a wide range of biological properties. They can be used as anticancer agents, antibacterial agents, and anti-tuberculosis drugs. In particular, trisubstituted 1,2,4-triazoles, which are important organic frameworks, exist in many pharmacologically active biomolecules. As shown in formula A, lavotidine (Lavoltidine) is a drug for the digestive system, mainly used for the treatment of peptic ulcer; JNJ-39393406 (shown in formula B) is an effective positive allosteric a7nAChR Regulator; Azamulin (as shown in formula C) is a kind of antibacterial, can be used for the treatment of acne; Pitrazepin (as shown in formula D) can interact with the emission receptor of central and peripheral nervous system, i...

Claims

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Application Information

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IPC IPC(8): C07D249/14A61P31/04A61P29/00A61P31/12A61P35/00A61P33/00A01N43/653A01P1/00A01P3/00A01P7/00
CPCA01N43/653A61P29/00A61P31/04A61P31/12A61P33/00A61P35/00C07D249/14
Inventor 郑绿茵陶开亮郭维
Owner GANNAN NORMAL UNIV
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