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Method for forming 1,5-subsituted triazole ring through catalyzing click by rare earth

A technology of rare earth catalysis and triazole ring, which is applied in the field of organic synthesis, can solve the problems of low mechanical strength and easy breaking of the polymer network, and achieve the effects of high biocompatibility, mild reaction conditions and high reaction yield

Inactive Publication Date: 2015-08-12
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the diffusion and the click reaction are almost synchronized, the formed polymer network has many defects, and even large particles of cuprous bromide exist in some places, and a large number of macropore defects appear in the polymer network, which makes the mechanical strength of the polymer network Not high, it is easy to break, limiting its application

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] a) Synthesis of terminal azido compounds: Accurately weigh 10 g of benzyl chloride and 12.8 g of sodium azide at room temperature and dissolve in 100 ml of organic solvent with a molar ratio of deionized water: acetone (1:3), and react at room temperature After reacting for 30 minutes, the reaction temperature was raised to 70 degrees Celsius, and the reaction time was 36 hours. Dilute the reacted product with 200ml of dichloromethane, and extract with saturated brine, dry the organic phase with magnesium sulfate overnight, pass the reaction product through a neutral alumina column, and spin dry with a rotary evaporator to obtain an oily liquid benzyl Azide 9.4g.

[0029] b) Synthesis of terminal alkynyl compounds: 5 g of propynyl alcohol was added to a round-bottomed sesame seed cake, distilled at 60 degrees Celsius under normal pressure, and the distilled fraction was taken out for later use.

[0030] The following is the use of rare earth metals to catalyze the clic...

Embodiment 2

[0034] The basic process is the same as in Example 1, the difference is that:

[0035] In step 1), the terminal azido propane azide is 0.16g (1.9mmol), 0.1g (1.7mmol) propynyl alcohol, 2uL 1mol / L rare earth metal compound neodymium nitrate solution, 2uL 1mol / L free radical initiator couple The N,N-dimethylformamide solution of nitrogen bisisobutyronitrile, under the protection of nitrogen, the reaction temperature is 60°C, and the reaction time is 20 minutes to form a 1,5-substituted triazole ring compound.

[0036] The rest are completely consistent with Example 1.

Embodiment 3

[0038] The basic process is the same as in Example 1, the difference is that:

[0039] In step 1), accurately weigh 0.2g (1.5mmol) benzyl azide compound and 0.1g (1.7mmol) propynyl alcohol, 2uL 1mol / L rare earth metal compound neodymium chloride solution, 2uL 0.5mol / L free radical initiation The N,N-dimethylformamide solution of azobisisobutyronitrile, under the protection of nitrogen, the reaction temperature is 60°C, and the reaction time is 15 minutes to form a 1,5-substituted triazole ring compound.

[0040] The rest are completely consistent with Example 1.

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Abstract

The invention discloses a method for forming a 1,5-subsituted triazole ring through catalyzing click by rare earth. The method comprises the following steps: generating a free radical from a free radical initiator at a certain temperature or under illumination, reducing high valence rare earth metal ions to form low valence rare earth metal ions, and synchronously catalyzing a click reaction of an alkynyl compound and a nitrine compound. The method allows one or more nitrine groups and one or more alkynyl groups to form the 1,5-triazole ring through using the controllability of the free radical initiation efficiency at a temperature or under illumination. The method for forming the 1,5-triazole ring has the advantages of simple operation, no need of ligands, easily available reaction materials, rapid reaction, mild reactions, short reaction time, structured structure of the 1,5-triazole ring, and high reaction yield.

Description

technical field [0001] The invention belongs to the field of organic synthesis methods and relates to a method for forming 1,5-substituted triazole rings by using rare earth catalyzed clicks. Background technique [0002] Due to the special structure of rare earth elements (rare earth elements have an unfilled 4f electron layer structure, and thus produce a variety of electronic energy levels), in organic synthesis, changes in their valence states can be used to achieve catalytic The role of the reaction process. [0003] "Click chemistry" is an organic synthesis method with fast chemical reaction, high yield, few by-products, mild reaction conditions and high stereoselectivity. It was proposed by Sharpless, the winner of the Nobel Prize in Chemistry in 2001, and its core is a new chemical synthesis method based on the heteroatom-containing link unit C-X-C. Since the method was proposed, it has received extensive attention in the fields of chemistry, biomedicine, polymer s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/04
CPCC07D249/04
Inventor 付国东邱亚文姚芳
Owner SOUTHEAST UNIV
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