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Method for synthesizing 1,2,3-triazole compound through one-pot two-step method

A compound and triazole technology, which is applied in the field of synthesis of 1,2,3-triazole compounds, can solve the problems of low yield, poor selectivity, cumbersome reaction steps and the like, and achieves simple process, convenient operation and simplification The effect of post-processing

Inactive Publication Date: 2017-04-26
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these synthetic methods all have some disadvantages, such as cumbersome reaction steps, low yield and poor selectivity, etc. The present invention aims to find a better method for synthesizing 1,2,3-triazoles

Method used

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  • Method for synthesizing 1,2,3-triazole compound through one-pot two-step method
  • Method for synthesizing 1,2,3-triazole compound through one-pot two-step method
  • Method for synthesizing 1,2,3-triazole compound through one-pot two-step method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Using different monovalent copper salts as catalysts, 1.0mmol iodobenzene, 1.2mmol sodium azide, 0.3mmol DBU and 0.2mmol catalyst were sequentially added to a reaction flask containing 5.0mL dimethyl sulfoxide, and the reaction mixture Stir the reaction at 95°C, track the reaction until the reaction is complete by TLC, add 1.0mmol phenylacetaldehyde (or phenylacetylene) to the reaction bottle after the reaction is cooled to room temperature, and add 50mL water to the reaction mixture and add a few drops of Ammonia, then extracted 3 times with dichloromethane, washed 1 time with saturated brine, dried, filtered with suction, removed solvent, and purified by column chromatography to obtain the target product. The influence of different catalysts on the reaction yield is shown in Table 1.

[0019] Table 1 Effect of different catalysts on reaction yield

[0020] Group catalyst temperature (℃) Reaction time (h) Yield (%) 1 CuI 95 / r.t. 2.5 / 0.5 92 ...

Embodiment 2

[0022] Add 1.0mmol of iodobenzene, 1.2mmol of sodium azide, 0.3mmol of DBU and 0.2mmol of cuprous iodide to a reaction flask containing 5.0mL of dimethyl sulfoxide, and stir the reaction mixture at 95°C for 2.5h , TLC followed the reaction until the reaction was complete. When the reaction was cooled to room temperature, 1.0mmol phenylacetaldehyde (or phenylacetylene) was added to the reaction bottle. After 0.5h of reaction, 50mL water was added to the reaction mixture and a few drops of ammonia water were added, and then Extracted three times with dichloromethane, washed once with saturated brine, dried, filtered with suction, spin off the solvent, and purified by column chromatography to obtain the target product with a yield of 92%.

[0023]

[0024] Data characterization of 1,4-diphenyl-1,2,3-triazole: off-white crystals; 1 H NMR (400 MHz, CDCl 3 ) δ : 8.20 (s, 1H), 7.95-7.89 (m, 2H), 7.82-7.77 (m, 2H), 7.55 (t, J = 7.7Hz,2H), 7.50-7.43 (m, 3H), 7.38 (t, J = 7.4 ...

Embodiment 3

[0026] Add 1.0mmol of iodobenzene, 1.2mmol of sodium azide, 0.1mmol of DBU and 0.1mmol of cuprous iodide to a reaction flask containing 5.0mL of dimethyl sulfoxide, and stir the reaction mixture at 95°C for 2.5h , TLC followed the reaction until the reaction was complete. When the reaction was cooled to room temperature, 1.0mmol phenylacetaldehyde (or phenylacetylene) was added to the reaction bottle. After 0.5h of reaction, 50mL water was added to the reaction mixture and a few drops of ammonia water were added, and then Extracted three times with dichloromethane, washed once with saturated brine, dried, filtered with suction, spin off the solvent, and purified by column chromatography to obtain the target product with a yield of 70%.

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Abstract

The invention discloses a method for synthesizing 1,2,3-triazole compound through a one-pot two-step method. An iodo-aryl compound, sodium azide, 1,8-diazabicyclo[5.4.0]-11-carbon-7-alkene and a catalyst cuprous iodide are added into a reaction container containing a solvent dimethyl sulfoxide, the reaction mixture is stirred and react at the temperature of 95 DEG C, and TLC tracking detection is carried out till reacting is complete; after the reaction temperature is reduced to room temperature, a phenylacetaldehyde compound or a terminal-based alkyne compound is added into the reaction container, after the reaction is completed, water and ammonium hydroxide are added into the reaction mixture, the extraction is carried out with dichloromethane three times, washing is carried out with saturated salt water once, drying and suction filtration are carried out, a solvent is spun out, column chromatography purification is carried out, and the target product is obtained. The method is simple in process, convenient to operate, mild in reaction condition, short in reaction time and high in target product yield.

Description

technical field [0001] The invention belongs to the technical field of synthesizing 1,2,3-triazole compounds, and in particular relates to a method for synthesizing 1,2,3-triazole compounds in one pot and two steps. Background technique [0002] There are too many heterocyclic compounds, which have always been the focus of research by chemists. Among them, 1,2,3-triazole compounds are a very important class of five-membered nitrogen-containing heterocyclic compounds, which have a special aromatic structure and strong stability. They will not be easily decomposed under strong acid and strong alkali conditions. Moreover, it is prone to various non-covalent bond interactions, such as strong ability to complex metal ions and hydrogen bonds. Therefore, 1,2,3-triazole is easy to combine with various enzymes and targets in organisms, thereby exhibiting various biological activities, such as anti-HIV, anti-tumor, antibacterial, anti-convulsant and anti-virus, etc., and is often use...

Claims

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Application Information

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IPC IPC(8): C07D249/06
CPCC07D249/06
Inventor 姜玉钦赵亚茹马素好李锡勇孙亚敏董文佩徐桂清
Owner HENAN NORMAL UNIV
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