Method of preparing 4,5-disubstituted 1,2,3-triazole with pyridinium salt

A technology of triazole and disubstituted, which is applied in the field of preparation of 1,2,3-triazole compounds, can solve the problems of difficulty in synthesizing olefins and cannot be purchased, and achieves the effects of simple synthesis operation and high yield

Inactive Publication Date: 2018-08-03
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

Synthesis of these alkenes is not easy and is not commercially available

Method used

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  • Method of preparing 4,5-disubstituted 1,2,3-triazole with pyridinium salt
  • Method of preparing 4,5-disubstituted 1,2,3-triazole with pyridinium salt
  • Method of preparing 4,5-disubstituted 1,2,3-triazole with pyridinium salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Ethyl α-bromoacetate (200mg, 1.2mmol) and pyridine (138mg, 1.8mmol) were dissolved in DMSO (5mL), stirred at room temperature for 5 hours. Then add benzaldehyde (191mg, 1.8mmol), NaN 3 (117mg, 1.8mmol) and L-proline (14mg, 0.12mmol), the reaction was stirred at room temperature. After the reaction was completed, the reaction solution was poured into ice water and extracted with ethyl acetate (20mL×4). The organic phases were combined, dried, and the solvent was removed under reduced pressure to obtain a crude product, which was separated and purified with a silica gel column to obtain 207 mg of the product, with a yield of 96%.

Embodiment 2

[0024] Ethyl α-bromoacetate (200mg, 1.2mmol) and pyridine (138mg, 1.8mmol) were dissolved in DMSO (5mL), stirred at room temperature for 5 hours. Then add benzaldehyde (191mg, 1.8mmol), NaN 3 (117mg, 1.8mmol) and serine (15mg, 0.12mmol), the reaction was stirred at room temperature. After the reaction was complete, the reaction solution was poured into ice water and extracted with ethyl acetate (20mL×4). The organic phases were combined, dried, and the solvent was removed under reduced pressure to obtain a crude product, which was separated and purified with a silica gel column to obtain 245mg of the product, with a yield of 94%.

Embodiment 3

[0026] Ethyl α-bromoacetate (200mg, 1.2mmol) and pyridine (138mg, 1.8mmol) were dissolved in DMSO (5mL), stirred at room temperature for 5 hours. Then add benzaldehyde (191mg, 1.8mmol), NaN 3 (117mg, 1.8mmol) and glycine (11mg, 0.12mmol), stirred at room temperature. After the reaction was completed, the reaction solution was poured into ice water and extracted with ethyl acetate (20mL×4). The organic phases were combined, dried and the solvent was removed under reduced pressure to obtain a crude product, which was separated and purified with a silica gel column to obtain 244 mg of the product, with a yield of 93%.

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Abstract

The invention relates to a method of synthesizing a 4,5-disubstituted 1,2,3-triazole compound. The method comprises the following step of by taking pyridine, halohydrocarbon, sulfonic ester, aldehydeand sodium azide as raw materials, and performing room-temperature reaction with a one-pot method. The synthetic method does not need a metal-containing catalyst, has the advantages of high yield of synthetic products, mild reaction condition, good functional group compatibility and the like, is simple in operation step, mild in reaction condition and wide in application range of a substrate, hasinnovativeness and a potential practical value and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemistry and chemical industry, and specifically relates to a preparation method of a 1,2,3-triazole compound. Background technique [0002] Triazole compounds are an important class of compounds that can be used in the fields of medicine, pesticide, dye, material science and catalysis, especially in the field of medicinal chemistry. Therefore, it is of scientific significance and application prospect to develop a simple method for synthesizing 1,2,3-triazole and its derivatives. The commonly used method is to use substituted alkynes or alkenes with electron-withdrawing substituents (one end of the alkene double bond is connected with NO2, CN, F, Cl, Br, I, etc.) to react with organic azide or sodium azide to synthesize 1,2,3-Triazoles and their derivatives. Although there are many reports of methods for synthesizing 1,2,3-triazole compounds, there are various problems and limitations (J.R.Johansson, T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06C07D401/04C07D409/04C07D249/04
CPCC07D249/06C07D249/04C07D401/04C07D409/04
Inventor 武钦佩武广龙
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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