Method for synthesizing selenium-containing triazole compound by using diselenide, acetylenic acid and nitrine

A synthesis method and technology of diselenide, applied in the field of synthesizing selenium-containing triazole compounds, can solve the problems of limited organic selenium sources, low reaction yield, complex extraction process, etc., achieve good application prospects, simple operation, The effect of easy access to raw materials

Inactive Publication Date: 2017-06-23
GUANGXI NORMAL UNIV
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  • Abstract
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Problems solved by technology

In addition, organic selenium compounds also play an important role in the development and development of agriculture and industry. However, due to the influence of many factors such as scarcity of selenium resources, extremely low content, complex extraction process, and high price, the source of organic selenium is limited, and its application is limited. very restrictive
Existing synthetic methods have disadvantages such as low reaction yield, poor reaction selectivity, high price, etc.

Method used

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  • Method for synthesizing selenium-containing triazole compound by using diselenide, acetylenic acid and nitrine
  • Method for synthesizing selenium-containing triazole compound by using diselenide, acetylenic acid and nitrine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 1-Benzyl-5-phenyl-4-(phenylselenyl)-1 H Synthesis of -1,2,3-triazole:

[0018] Add 0.5 mmol of phenylpropylic acid, 0.5 mmol of diphenyldiselenide, 0.5 mmol of benzyl azide, 10 mol% anhydrous copper sulfate, 0.6 mmol of potassium carbonate and 3 mL of toluene to the sealed tube, at 120 o The reaction was carried out at C for 6 h, and the reaction was monitored by TLC; after the reaction was complete, it was cooled to room temperature, the solvent was removed under reduced pressure, and purified by flash silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain the yellow solid product 1a, the product The rate is 80%, and its structural formula is, ;

[0019] Product characterization: 1 H NMR (400 MHz, CDCl 3 ) δ 8.06 – 8.04 (m, 2H), 7.43 – 7.33 (m,3H), 7.23 – 7.21 (m, 5H), 7.18 – 7.08 (m, 3H), 7.01 – 6.94 (m, 2H), 5.66 (s ,2H). 13 C NMR (100 MHz, CDCl 3 ) δ 151.5, 134.8, 130.5, 129.6, 129.5, 129.2, 128.6, 128.5, 128.4, 128.1, 127.9, 127...

Embodiment 2

[0021] 1-Benzyl-5-(4-methylphenyl)-4-(phenylselenyl)-1 H Synthesis of -1,2,3-triazole:

[0022] Add 0.5 mmol p-tolylpropiolic acid, 0.5 mmol diphenyldiselenide, 0.5 mmol benzyl azide, 10 mol% anhydrous copper acetate, 0.6 mmol potassium hydroxide and 3 mL xylene at 120 o The reaction was carried out at C for 6 h, and the reaction was monitored by TLC; after the reaction was complete, it was cooled to room temperature, the solvent was removed under reduced pressure, and purified by flash silica gel column chromatography (petroleum ether:ethyl acetate=10:1) to obtain the yellow solid product 1b, which was produced as The rate is 68%, and its structural formula is,

[0023] ;

[0024] Product characterization: 1 H NMR (400 MHz, CDCl 3 ) δ 7.94 (d, J = 8.1 Hz, 2H), 7.27 – 7.12(m, 7H), 7.12 – 7.00 (m, 3H), 6.97 – 6.89 (m, 2H), 5.60 (s, 2H), 2.32 (s,3H). 13 C NMR (100 MHz, CDCl 3 ) δ 151.5, 138.3, 134.7, 129.6, 129.5, 129.0, 128.9, 128.5, 128.0, 127.7, 127.5, 127.1, 127....

Embodiment 3

[0026] 1-Benzyl-5-(2-naphthyl)-4-(phenylselenyl)-1 H Synthesis of -1,2,3-triazole:

[0027] Add 0.5 mmol of 2-propynenaphthoic acid, 0.5 mmol of diphenyldiselenide, 0.5 mmol of benzyl azide, 10 mol% of copper chloride, 0.6 mmol of sodium carbonate and 3 mL of chloride to the sealed tube Benzene, at 120 o The reaction was carried out at C for 6 h, and the reaction was monitored by TLC; after the reaction was complete, it was cooled to room temperature, the solvent was removed under reduced pressure, and purified by flash silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain the yellow solid product 1c, which was produced The rate is 60%, and its structural formula is, ;

[0028] Product characterization: 1 H NMR (400 MHz, CDCl 3 ) δ 8.52 (s, 1H), 8.23 ​​– 8.20 (m, 1H), 7.92 – 7.73 (m, 3H), 7.44 – 7.41 (m, 2H), 7.21 – 7.18 (m, 5H), 7.12 – 6.89(m , 5H), 5.65 (s, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ 151.3, 134.7, 133.1, 129.6, 129.5, 129.3, 128...

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Abstract

The invention discloses a method for synthesizing a selenium-containing triazole compound by using diselenide, acetylenic acid and nitrine. The synthesis method comprises the following steps: adding 0.5 mmol of acetylenic acid, 0.5 mmol of diselenide, 0.5 mmol of benzyl azide, 10 percent of a Cu catalyst (such as anhydrous cupric sulfate, copper acetate, copper chloride, cuprous chloride or cuprous iodide), 0.6 mmol of alkali (such as potassium carbonate, potassium hydroxide, sodium carbonate, potassium tert-butoxide and cesium carbonate and 3 mL of a solvent (such as methylbenzene, xylene or chlorobenzene into a sealed tube, reacting at a temperature of 120 DEG C for 6 hours and performing TLC tracking reaction; after the reaction is conducted completely, cooling to a room temperature, reducing pressure to remove the solvent, and performing rapid silica gel column chromatography purification (the ratio of petroleum ether to ethyl acetate is equal to 10:1) to obtain a product. The selenium-containing triazole compound is synthesized by using the three components, namely the diselenide, the acetylenic acid and the nitrine, under the action of the copper catalyst through a one-pot method. According to the method, the raw materials are easily available, the method is simple in operation, the yield is considerable and the application prospect is good.

Description

technical field [0001] The invention relates to the synthesis of triazole compounds, in particular to a method for synthesizing selenium-containing triazole compounds by using a three-component one-pot method of diselenide, alkynoic acid and azide. Background technique [0002] Selenium is a component of selenoproteins and selenium-containing enzymes in the human body, and has many functions such as anti-oxidation and maintaining normal immunity. The general method of supplementing selenium is to make oral preparations with inorganic selenium compounds. Studies have shown that organic selenium compounds have low toxicity and are more significant than inorganic selenium in stimulating immune responses. In addition, organic selenium compounds also play an important role in the development and development of agriculture and industry. However, due to the influence of many factors such as scarcity of selenium resources, extremely low content, complex extraction process, and high ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06
CPCC07D249/06
Inventor 陈静徐燕丽潘英明崔飞虎王恒山
Owner GUANGXI NORMAL UNIV
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