Method for synthesizing 1,2,3-triazole compounds by utilizing sila-alkyne compounds

A technology of silicon-based alkynes and compounds, which is applied in the field of preparation of triazole compounds, can solve problems such as limitations, and achieve the effects of avoiding the use of heavy metals, simple process, and high yield

Inactive Publication Date: 2012-02-01
HAINAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Undoubtedly, terminal alkynes are required to be used in the above methods, and the source and preparation of ra

Method used

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  • Method for synthesizing 1,2,3-triazole compounds by utilizing sila-alkyne compounds
  • Method for synthesizing 1,2,3-triazole compounds by utilizing sila-alkyne compounds
  • Method for synthesizing 1,2,3-triazole compounds by utilizing sila-alkyne compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Preparation of 1,5-diphenyl-1,2,3-triazole

[0019]

[0020] Add 174 mg (1 mmol) of trimethylsilylphenylacetylene, 119 mg (1 mmol) of phenyl azide, and 2 mL of dimethyl sulfoxide into the reactor, keep the reaction temperature at 30 ° C, and add the desilication reagent KOH into the reaction system 73mg (1.3mmol), start stirring, and continue to react until thin plate chromatography shows that the raw material disappears. Then 6 mL of saturated ammonium chloride solution and 50 mL of ethyl acetate were added, and the mixture was transferred to a separatory funnel, washed four times with 50 mL of water, and once with 20 mL of saturated brine. Anhydrous Na for organic phase 2 SO 4 dry. Filtration, removal of solvent under reduced pressure and column chromatography yielded the title compound. Yield, 85%. The NMR data are as follows:

[0021] 1 H NMR (CDCl 3 , 400MHz): δ7.19-7.24(m, 2H), 7.30-7.38(m, 5H), 7.40-7.46(m, 3H), 7.86(s, 1H); 13 C NMR (CDCl 3 , 100MHz...

Embodiment 2

[0023] Preparation of 1-(4-methylphenyl)-5-phenyl-1,2,3-triazole

[0024]

[0025] Add 174 mg (1 mmol) of trimethylsilylphenylacetylene, 134 mg (1 mmol) of 4-methylphenyl azide, and 2 mL of dimethyl sulfoxide into the reactor, keep the reaction temperature at 30 ° C, and add Silicon-based reagent KOH 73mg (1.3mmol), start stirring, and continue the reaction until thin plate chromatography shows that the raw material disappears. Then 6 mL of saturated ammonium chloride solution and 50 mL of ethyl acetate were added, and the mixture was transferred to a separatory funnel, washed four times with 50 mL of water, and once with 20 mL of saturated brine. Anhydrous Na for organic phase 2 SO 4 dry. Filtration, removal of solvent under reduced pressure and column chromatography yielded the title compound. Yield, 83%. The NMR data are as follows:

[0026] 1 H NMR (CDCl 3 , 400MHz): δ2.35(s, 3H), 7.09-7.18(m, 4H), 7.35-7.42(m, 2H), 7.43-7.46(m, 3H), 7.83(s, 1H); 13 C NMR (CDCl...

Embodiment 3

[0028] Preparation of 1-(4-methoxyphenyl)-5-phenyl-1,2,3-triazole

[0029]

[0030] Add 174 mg (1 mmol) of trimethylsilylphenylacetylene, 150 mg (1 mmol) of 4-methoxyphenyl azide, and 2 mL of dimethyl sulfoxide into the reactor, keep the reaction temperature at 30 ° C, and add Desilication reagent KOH 73mg (1.3mmol), start stirring, continue to react until the thin plate chromatography shows that the raw material disappears. Then 6 mL of saturated ammonium chloride solution and 50 mL of ethyl acetate were added, and the mixture was transferred to a separatory funnel, washed four times with 50 mL of water, and once with 20 mL of saturated brine. Anhydrous Na for organic phase 2 SO 4 dry. Filtration, removal of solvent under reduced pressure and column chromatography yielded the title compound. Yield, 80%. The NMR data are as follows:

[0031] 1 H NMR (CDCl 3 , 400MHz): δ3.83(s, 3H), 6.92(d, J=2H), 7.21-7.30(m, 4H), 7.31-7.38(m, 3H), 7.85(s, 1H); 13 C NMR (CDCl 3, 1...

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Abstract

The invention relates to a method for synthesizing 1,2,3-triazole compounds by utilizing sila-alkyne compounds. The method comprises the following steps of: adding a sila-alkyne compound, an azide, an organic solvent and a desilication reagent to a reactor, and reacting at the temperature of 10-100 DEG C; and after the reaction is finished, adding an inorganic acid aqueous solution for acidifying until the pH value presents acidity, extracting multiple times with ethyl acetate, washing organic phase with saturated saline solution, drying with anhydrous sodium sulfate, removing the solvent under reduced pressure, and separating and purifying the residue through recrystallizing or column chromatography to obtain a product. The method has the advantages that the process is simple; the sila-alkyne compounds are used as raw material, thereby avoiding the use of heavy metals; the raw materials and reagents are available; the method has the characteristics of mild reaction condition, no need of carrying out oxygen-free protection on the reaction system, high reaction selectivity, high yield and the like; and the method has important practical significance.

Description

technical field [0001] The invention relates to a method for preparing triazole compounds, in particular to a method for synthesizing 1,2,3-triazole compounds by using silicon-based alkyne compounds. Background technique [0002] 1,2,3-Triazole compounds are an important class of heterocyclic compounds. Although they do not exist in nature, triazole compounds have been shown in medicine, pesticides and dyes since they were synthesized and discovered. It has an important application value, especially in the development of medicine, and a variety of structures with good biological activities have been found. Therefore, the development of 1,2,3-triazole compounds and the development of synthetic methods have received extensive attention. [0003] At present, the Huisgen cycloaddition reaction of alkynes and azides is undoubtedly the most widely used method in the synthesis of 1,2,3-triazoles [1,3-Dipolar Cycloaddition Chemistry New York: Wiley.vol.1:1- 176, 1984]. However, t...

Claims

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Application Information

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IPC IPC(8): C07D249/06
Inventor 吴禄勇陈光英宋小平陈昱学宋鑫明唐蜜苟铨
Owner HAINAN NORMAL UNIVERSITY
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