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A kind of synthetic method of 1,2,3-triazole derivatives substituted at n1 position

A synthesis method and derivative technology, applied in the direction of organic chemistry, can solve the problems of large environmental damage, poor safety, and high equipment requirements, and achieve the effect of wide application range, good substrate universality, and wide substrate range.

Active Publication Date: 2021-02-26
江苏安杰泰生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, the most common method for synthesizing such compounds is the 1,3-dipolar cycloaddition reaction of azides and alkynes, but an important defect of this method is that highly toxic azides need to be used during synthesis. Raw materials, so the safety is poor, the damage to the environment is greater and the equipment requirements are higher

Method used

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  • A kind of synthetic method of 1,2,3-triazole derivatives substituted at n1 position
  • A kind of synthetic method of 1,2,3-triazole derivatives substituted at n1 position
  • A kind of synthetic method of 1,2,3-triazole derivatives substituted at n1 position

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Experimental program
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Effect test

Embodiment 1

[0025] Synthesis of 1,2,3-triazole derivatives substituted at N1 position:

[0026]

[0027] Add benzyl bromide (1.0mmol), 1H-1,2,3-triazole (1.0mmol), Cu 2 O (0.1mmol), DMEDA (0.2mmol), K 2 CO 3 (1.2mmol), then add solvent toluene 2mL, react at room temperature for 8 hours, concentrate the reaction solution after the end of the reaction, and separate by column chromatography to obtain the corresponding product 1 with an isolated yield of 88%. 1 H NMR (400MHz, CDCl 3 )δ:7.86-7.78(m,2H),7.70(d,J=7.2Hz,1H),7.64(d,J=7.0Hz,1H),7.38-7.30(m,3H),5.61(s,2H ). HRMS theoretical value: C 9 h 9 N 3 (M+H) + : 160.0875, actual measured value: 160.0879.

Embodiment 2

[0029] Synthesis of 1,2,3-triazole derivatives substituted at N1 position:

[0030]

[0031] Add 4-methylbenzyl bromide (1.2mmol), 1H-1,2,3-triazole (1.0mmol), Cu 2 O (0.1mmol), DMEDA (0.2mmol), K 2 CO 3 (1.5mmol), then add solvent toluene 2mL, react at room temperature for 8 hours, concentrate the reaction solution after the end of the reaction, and separate by column chromatography to obtain the corresponding product 2 with an isolated yield of 91%. 1 H NMR (400MHz, CDCl 3 )δ: 7.80-7.71 (m, 4H), 7.66 (d, J = 7.2Hz, 1H), 7.62 (d, J = 7.0Hz, 1H), 5.65 (s, 2H), 2.23 (s, 3H). HRMS theoretical value: C 10 h 11 N 3 (M+H) + : 174.1031, actual measured value: 174.1036.

Embodiment 3

[0033] Synthesis of 1,2,3-triazole derivatives substituted at N1 position:

[0034]

[0035] Add 2-methylbenzyl bromide (1.2mmol), 1H-1,2,3-triazole (1.0mmol), Cu 2 O (0.1mmol), DMEDA (0.2mmol), K 2 CO 3 (1.5mmol), and then added solvent tetrahydrofuran 2mL, and reacted at room temperature for 12 hours. After the reaction, the reaction solution was concentrated and separated by column chromatography to obtain the corresponding product 3 with an isolated yield of 93%. 1 H NMR (400MHz, CDCl 3 )δ: 7.82-7.75 (m, 4H), 7.67 (d, J = 7.0Hz, 1H), 7.62 (d, J = 7.0Hz, 1H), 5.67 (s, 2H), 2.20 (s, 3H). HRMS theoretical value: C 10 h 11 N 3 (M+H) + : 174.1031, actual measured value: 174.1034.

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Abstract

The invention relates to a method for synthesizing 1,2,3-triazole derivatives substituted at the N1 position. The method comprises: using cuprous oxide as a catalyst and using N,N'-dimethylethylenediamine as a ligand , catalyzing the reaction of 1H-1,2,3-triazole with halogenated hydrocarbons in an organic solvent to obtain 1,2,3-triazole derivatives substituted at the N1 position. Compared with the prior art, the synthesis process of the present invention is simple and green, has excellent selectivity and higher yield, and has a wide range of substrates. The method of the present invention has great applications in the synthesis of medicines, natural products, etc. potential.

Description

technical field [0001] The invention belongs to the technical field of synthetic chemistry and relates to a synthesis method of 1,2,3-triazole derivatives substituted at N1 position. Background technique [0002] N1-substituted 1,2,3-triazole derivatives are an important class of five-membered nitrogen-containing heterocyclic compounds, and their skeletons are widely used in a variety of drug molecules, such as rufinamide carboxamide triazole and so on. Therefore, it is of great significance to find an effective method to synthesize N1-substituted 1,2,3-triazole derivatives. [0003] At present, the most common method for synthesizing this type of compound is the 1,3-dipolar cycloaddition reaction of azide compound and alkyne, but an important defect of this type of method is that it needs to use highly toxic azide as Raw materials, so the safety is poor, the damage to the environment is greater and the requirements for equipment are higher. [0004] Therefore, designing a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/04
CPCC07D249/04
Inventor 姚子健吕文瑞李荣建高永红邓维
Owner 江苏安杰泰生物科技有限公司
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