Copper-free Click reaction catalysis system and application thereof

A catalytic system and reaction technology, applied in physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, organic chemistry, etc., can solve the problems of unreported applications, application limitations, and inability to prepare, etc., to achieve Avoid the use of toxic solvents, good substrate applicability, and easy preparation

Inactive Publication Date: 2019-04-26
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The Sharpless and Medal groups found that the copper-catalyzed dipolar cycloaddition reaction of terminal alkynes and azides (CuAAC reaction) can efficiently prepare 1,4-substituted 1,2,3-triazoles under mild conditions, but However, 1,4,5-multi-substituted 1,2,3-triazoles cannot be prepared
In addition, the application of copper-promoted CuAAC reactions in bioorthogonal reactions is limited due to the biotoxicity of metallic copper.
In recent years, the synergistic effect of anion and cation in ionic liquids makes them show good catalytic activity in many organic reactions, but their application in metal-free catalyzed Click reactions has not been reported yet.

Method used

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  • Copper-free Click reaction catalysis system and application thereof
  • Copper-free Click reaction catalysis system and application thereof
  • Copper-free Click reaction catalysis system and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] Take 0.20mmol of m-methoxybenzyl azide and 0.20mmol of ethyl acetoacetate in a dry reaction flask, then add 0.20mmol of ionic liquid A2B5, stir and react at 50°C for 2h, the reaction process is detected by TLC, after the reaction The crude product was extracted and spin-dried with a mixed solvent of ethyl acetate and distilled water at a volume ratio of 1:1, and the crude product was separated by silica gel column chromatography to obtain the target product with an isolated yield of 91%.

Embodiment 2

[0027]

[0028] Take 0.20mmol of p-methoxybenzyl azide and 0.20mmol of ethyl acetoacetate in a dry reaction flask, then add 0.20mmol of ionic liquid A2B5, stir and react at 50°C for 2h, the reaction process is detected by TLC, after the reaction The crude product was extracted and spin-dried with a mixed solvent of ethyl acetate and distilled water at a volume ratio of 1:1, and the crude product was separated by silica gel column chromatography to obtain the target product with an isolated yield of 92%.

Embodiment 3

[0030]

[0031] Take 0.20mmol of o-methoxybenzyl azide and 0.20mmol of ethyl acetoacetate in a dry reaction flask, then add 0.20mmol of ionic liquid A1B3, stir and react at 50°C for 2h, the reaction process is detected by TLC, after the reaction is completed The crude product was extracted and spin-dried with a mixed solvent of ethyl acetate and distilled water at a volume ratio of 1:1, and the crude product was separated by silica gel column chromatography to obtain the target product with an isolated yield of 85%.

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Abstract

The invention discloses a copper-free Click reaction catalysis system and application thereof, and belongs to the technical field of Click reaction catalysis systems. According to the key points of the technical scheme, the copper-free Click reaction catalysis system is ionic liquid, positive ions in the ionic liquid are shown in a formula (please see the specifications for the formula), and negative ions in the ionic liquid are shown in a formula (please see the specifications for the formula). The invention further specifically discloses the application of the copper-free Click reaction catalysis system to promote a copper-free Click reaction to prepare a 1,4,5-substituted-1,2,3-triazole compound. The applied catalysis system ionic liquid is easy and convenient to prepare, low in cost and easy to obtain and has mild acid and alkaline; the reaction system is carried out under the solvent-free condition, and thus use of toxic solvents is effectively avoided; and the catalysis system can be recycled for several times, and the catalytic activity of the catalysis system remains unchanged basically.

Description

technical field [0001] The invention belongs to the technical field of Click reaction catalytic systems, and in particular relates to a copper-free Click reaction catalytic system and its application. Background technique [0002] In the past few years, molecules containing 1,2,3-triazole structures have been found to have broad-spectrum antiviral, antibacterial, antifungal and anticancer biological activities, such as tetracyclic 1,2,3-triazole Azole compounds showed good serine protease inhibitory activity; nucleoside derivative tert-butyldimethylsilylspiroaminooxythiodioxide was identified as a potent non-nucleoside reverse transcriptase inhibitor. Furthermore, the applications of 1,2,3-triazoles are not limited to drug discovery, but are also heavily used in many other research fields, such as bioconjugation, macromolecular chemistry, and polymer science. [0003] The classic Huisgen 1,3-dipolar cycloaddition reaction uses terminal alkyne and azide as raw materials to o...

Claims

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Application Information

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IPC IPC(8): B01J31/02C07D249/06
CPCB01J31/0279C07D249/06
Inventor朱安莲王静怡李凌君
OwnerHENAN NORMAL UNIV