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Method for synthesizing NH-1,2,3-triazole

A synthesis method and azide technology, applied in organic chemistry and other directions, can solve the problems of harsh conditions, many reaction steps, and difficult to obtain raw materials, and achieve the effects of mild reaction conditions, low production cost, and wide application range.

Inactive Publication Date: 2015-01-28
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These N H The synthesis method of -1,2,3-triazole has many disadvantages, such as many reaction steps, difficult to obtain raw materials, harsh conditions, limited range of substrates, low yield, and unsuitable for large-scale production.

Method used

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  • Method for synthesizing NH-1,2,3-triazole
  • Method for synthesizing NH-1,2,3-triazole
  • Method for synthesizing NH-1,2,3-triazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1: Preparation of 4-phenyl-N by β-nitrostyrene H -1,2,3-Triazole

[0019]

[0020] To a 250 mL round bottom flask, add β-nitrostyrene (10.5 g, 70 mmol), NaN 3 (5.5g, 84mmol) and 100mL N,N-dimethylformamide, then added p-toluenesulfonic acid (3.3g, 21mmol), heated to 60 ℃ in the air to react, the reaction was detected by thin layer chromatography, and the reaction After completion, it was cooled to room temperature, the reaction mixture was extracted with ethyl acetate and water, the organic phases were combined and spin-dried in vacuo, the reaction crude product was separated by recrystallization or column chromatography to obtain 9.4g of pure product, the product was a white solid, and the yield 93%.

[0021] structural analysis

[0022] 1 H NMR (DMSO- d 6 , 400 MHz), 1 drop TFA : δ 15.19 (s, 1 H), 8.35 (s, 1 H), 7.87 (d, J = 6.8 Hz, 2 H), 7.44 (d, J = 7.2 Hz, 2 H ), 7.35 (d, J = 6.8 Hz, 1 H); 13 C NMR (DMSO- d 6 , 100 MHz) , 1 drop TFA: δ 145.3, ...

Embodiment 2

[0024] Example 2: Preparation of 4-methoxyphenyl-N by β-nitro-p-methoxystyrene H -1,2,3-Triazole

[0025]

[0026] To a 10mL round bottom flask, add β-nitro-p-methoxystyrene (53.7 mg, 0.3mol), NaN 3 (29.3 mg, 0.45mmol) and 3mL N,N-dimethylformamide, then added p-toluenesulfonic acid (25.8 mg, 0.15mmol), heated to 60°C in air to react, and detected the reaction by thin layer chromatography, After the reaction was completed, it was cooled to room temperature, the reaction mixture was extracted with ethyl acetate and water, the organic phases were combined and spin-dried in vacuo, the reaction crude product was separated by recrystallization or column chromatography to obtain 50.9 mg of pure product, the product was a white solid, Yield 97%.

[0027] Structural analysis: 1 H NMR (DMSO- d 6 , 400 MHz), 1 drop TFA: δ 8.22 (s, 1 H), 7.79 (d, J = 8.4 Hz, 2 H), 7.01 (d, J = 8.8 Hz, 2 H), 3.77 (s, 3 H ). 13 C NMR (DMSO- d 6 , 100 MHz), 1 drop TFA: δ 159.4, 144.9, 127.1, 12...

Embodiment 3

[0029] Example 3: Preparation of 2,4-dichlorophenyl-N from β-nitro 2,4-dichlorostyrene H -1,2,3-Triazole

[0030]

[0031] To a 10 mL round bottom flask, add β-nitro 2,4-dichlorostyrene (65.1 mg, 0.3 mmol), NaN 3 (29.3mg, 0.45mmol) and 3mL N,N-dimethylformamide, then added p-toluenesulfonic acid (25.8 mg, 0.15mmol), heated to 60°C in air to react, and detected the reaction by thin layer chromatography, After the reaction was completed, it was cooled to room temperature, and the reaction mixture was extracted with ethyl acetate and water. The organic phases were combined and spin-dried in vacuo. The reaction crude product was separated by recrystallization or column chromatography to obtain 57.5 mg of pure product. The product was a white solid. Yield 90%.

[0032] Structural analysis: 1 H NMR (DMSO- d 6 , 400 MHz), 1 drop TFA: δ 8.41 (s, 1 H), 7.96 (d, J = 8.0 Hz, 1 H), 7.72 (s, 1 H), 7.52 (d, J = 8.4 Hz, 1 H ). 13 C NMR (DMSO- d 6 , 100 MHz), 1 drop TFA: δ 141.6,...

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Abstract

The invention discloses a method for synthesizing NH-1,2,3-triazole shown by a formula (I). Under the catalytic action of a Lewis acid catalyst, nitroalkene shown by a formula (II) and hydrazoic acid salt undergo 1,3-dipolar cycloaddition, wherein Ar is phenyl, substituted phenyl, naphthyl, furyl, thienyl, indolyl or styryl; and R is hydrogen atom, phenyl, substituted phenyl or C1-C6 alkyl. The method is mild in reaction condition, low in production cost, wide in substrate application range and high in yield, and provides a new path for synthesizing NH-1,2,3-triazole compounds with medicinal activity.

Description

technical field [0001] The present invention relates to a kind of N H The synthetic method of -1,2,3-triazole is a kind of suitable for large-scale production of N H A simple and efficient synthesis method for 1,2,3-triazole belongs to the technical field of organic synthesis. Background technique [0002] In the modern pharmaceutical and pesticide industries, N H -1,2,3-Triazoles are widely used in the preparation of organic heterocyclic intermediates and drug synthesis. In medicine, N H -1,2,3-Triazole itself is an important pharmacophore and can be used as an inhibitor of human methionine aminopeptidase (hMetAP2), indoleamine 2,3-dioxygenase (IDO), etc. , and it is also the basic skeleton of many bioactive molecules. Traditional Synthesis N H -1,2,3-triazole methods mainly include (1) copper-catalyzed "click reaction" of alkyne with trimethylsilyl azide and (2) palladium-catalyzed β-bromocycloethylene with sodium azide coupling reaction. These N H The synthesis m...

Claims

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Application Information

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IPC IPC(8): C07D249/06C07D405/04C07D409/04C07D403/04C07D249/04C07D491/052
CPCC07D249/04C07D249/06C07D403/04C07D405/04C07D409/04C07D491/052
Inventor 关正辉权雪静任智卉
Owner NORTHWEST UNIV
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