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Method for preparing triazole derivatives

A derivative, triazole technology, applied in the field of preparation of triazole derivatives, can solve the problems of cumbersome steps, complex reaction conditions, low yield, etc., and achieve wide applicability, high yield, and easy operation Effect

Pending Publication Date: 2019-03-19
HENAN NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] So far, scientific researchers have discovered many synthetic methods of triazole compounds, but most of the synthetic methods have cumbersome steps, complicated reaction conditions and low yields.

Method used

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  • Method for preparing triazole derivatives
  • Method for preparing triazole derivatives
  • Method for preparing triazole derivatives

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preparation example Construction

[0029] Preparation of compound 1:

[0030]

Embodiment 1

[0032] Dissolve p-toluenesulfonyl azide (1.0mmol), phenylacetylene (1.1mmol), o-aminophenol (0.2mmol), cuprous iodide (0.1mmol) in 1mL acetonitrile, react at room temperature for 3h, add 2mL Saturated ammonium chloride quenched the reaction, added 30 mL of water, extracted with 40 mL of dichloromethane × 3, collected the organic phase, dried over anhydrous sodium sulfate, removed the solvent by rotary evaporation under reduced pressure, and separated by silica gel column chromatography to obtain a white solid with a yield of 32 %.

[0033] 1 H NMR (400MHz, CDCl3): δ8.32(s, 1H), 8.03(d, J=8.4Hz, 2H), 7.82(d, J=7.2Hz, 2H), 7.45–7.38(m, 5H), 2.44(s,3H).

Embodiment 2

[0035] Dissolve p-toluenesulfonyl azide (1.0mmol), phenylacetylene (1.1mmol), o-aminophenol (0.1mmol), cuprous iodide (0.1mmol) in 1mL acetonitrile, react at room temperature for 3h, add 2mL Saturated ammonium chloride quenched the reaction, adding water 30mL, dichloromethane 40mL×3 for extraction, collected the organic phase, dried over anhydrous sodium sulfate, removed the solvent by rotary evaporation under reduced pressure, and separated by silica gel column chromatography to obtain a white solid with a yield of 38 %.

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Abstract

The invention discloses a method for preparing triazole derivatives. The method comprises the following steps: taking aryl sulfonyl azide derivatives and acetylenic derivatives as raw materials, taking cuprous iodide and ortho-aminophenol as catalysts, and carrying out a cyclization reaction under the condition of an aprotic polar solvent, thereby obtaining the triazole derivatives. According to the method for preparing triazole derivatives disclosed by the invention, the reaction substrate is wide in universality, and the method is mild in reaction conditions, simple and convenient to operateand high in yield.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of triazole derivatives. Background technique [0002] As a very valuable five-membered nitrogen-containing heterocyclic skeleton, triazole derivatives are widely used in organic catalysis, materials science and other fields due to their excellent optical and anti-corrosion properties. In addition, the good biological activity of the triazole derivatives also has important applications in the pharmaceutical industry and pesticides. Therefore, the synthesis and application of triazole compounds have received extensive attention. [0003] So far, scientific researchers have discovered many synthetic methods of triazole compounds, but most of the synthetic methods have cumbersome steps, complicated reaction conditions and low yields. Therefore, it is very necessary to develop a method with wide universality of reaction substrates, mild reaction con...

Claims

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Application Information

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IPC IPC(8): C07D249/06C07D409/04C07D409/12
CPCC07D249/06C07D409/04C07D409/12
Inventor 毕晶晶张继昊谭强李青李颖黄心洁
Owner HENAN NORMAL UNIV
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