Method for synthesizing 1, 4-bis-substituted-1, 2, 3-triazole by cycloaddition reaction of base catalysis enaminone and sulfonyl azide

A technology of base-catalyzed enaminones and sulfonyl azide rings, which is applied in the direction of organic chemistry and the like, and achieves the effects of cheap and easy-to-obtain raw materials, wide application prospects, and environmental friendliness.

Active Publication Date: 2016-12-07
JIANGXI NORMAL UNIV
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  • Abstract
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Problems solved by technology

Interestingly, the synthesis of 1,4-disubstituted 1,2,3-triazoles via N–N bond cleavage reactions in enaminones and sulfonyl azides has not been reported yet.

Method used

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  • Method for synthesizing 1, 4-bis-substituted-1, 2, 3-triazole by cycloaddition reaction of base catalysis enaminone and sulfonyl azide
  • Method for synthesizing 1, 4-bis-substituted-1, 2, 3-triazole by cycloaddition reaction of base catalysis enaminone and sulfonyl azide
  • Method for synthesizing 1, 4-bis-substituted-1, 2, 3-triazole by cycloaddition reaction of base catalysis enaminone and sulfonyl azide

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Embodiment Construction

[0017] The present invention is achieved by N,N-dimethyl substituted amino enaminone 1 (0.3mmol), primary amine 2 (0.4mmol) and FeCl 3 (0.15 mmol) was placed in a dry 25 mL round bottom flask, then 2 mL of acetonitrile was added, and stirred at room temperature for 2 hours. Sulfonyl azide 3 (0.4 mmol) and sodium tert-butoxide (0.45 mmol) were then added and stirring was continued at room temperature for 2 hours. After the reaction was completed, 5 mL of water was added to the flask, and the resulting mixture was extracted with ethyl acetate (3×8 mL), and the organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent in the filtrate was removed under reduced pressure, and the residue was purified by silica gel column chromatography and washed with ethyl acetate:petroleum ether (6:1) mixture to obtain the target product 4. The structure and purity of all products were confirmed by nuclear magnetic resonance, high-resolution mass spect...

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Abstract

The invention discloses a method for synthesizing 1, 2, 3-triazole by cycloaddition reaction of base catalysis enaminone and azide. According to the method, propargyl esters, primary amine and sulfonyl azide serve as raw materials, the enaminone with an NH structure is generated in situ, the raw materials are stirred at room temperature for two hours under catalysis of secondary amine and sodium tert-butoxide, 1, 4-bis-substituted-1, 2, 3-triazole compounds can be obtained with high yield, and products are subjected to chromatographic purification by a silica gel column. The method has the advantages that reaction conditions are mild, reaction can be smoothly realized at the room temperature, reaction time is short, two steps can be finished totally for four hours, the raw materials are green and low in cost, ferric chloride used in first-step operation is an environment-friendly catalyst, metal is omitted in second-step reaction, the method is greener than most methods for synthesizing similar compounds, and the method is simple in overall operation and suitable for large-scale production.

Description

technical field [0001] The invention relates to a method for synthesizing 1,4-disubstituted-1,2,3-triazole by base-catalyzed enaminone and sulfonyl azide cycloaddition reaction. Background technique [0002] 1,2,3-Triazoles are common basic structures of heterocyclic compounds, which have important application value in many fields such as biomedicine, materials, and chemical intermediates. Since Sharpless et al. synthesized 1,2,3-triazoles by direct cycloaddition reaction of azides and alkynes via copper catalysis and proposed the concept of "click chemistry" based on the reaction, the synthesis of such compounds and Applied research has made unprecedented progress. In addition to the copper-catalyzed click cycloaddition reaction, other transition metals such as rhodium, ruthenium, iridium, etc. can also be used to catalyze this type of cycloaddition reaction to synthesize 1,2,3-triazole. - triazole compounds. With the current increasing emphasis on sustainable developmen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06C07D409/06
CPCC07D249/06C07D409/06
Inventor 刘云云万结平曹硕
Owner JIANGXI NORMAL UNIV
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