Method for synthesizing 1-substituted-1, 2, 3-triazole from sodium acetylide

A technology of sodium acetylene and triazole, applied in the field of synthesizing 1-substituted-1,2,3-triazole, achieving effective synthesis method, simple operation, fast and efficient reaction

Inactive Publication Date: 2011-05-11
TONGJI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The biggest drawback of this method is to use precious metals to complete

Method used

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  • Method for synthesizing 1-substituted-1, 2, 3-triazole from sodium acetylide
  • Method for synthesizing 1-substituted-1, 2, 3-triazole from sodium acetylide
  • Method for synthesizing 1-substituted-1, 2, 3-triazole from sodium acetylide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Synthesis of 1-p-tolyl-1,2,3-triazole

[0025]

[0026] Dimethyl sulfoxide (3 mL), p-tolyl azide (0.3 mmol), and sodium acetylide (2.1 mmol) were added to the reactor, and the reaction was performed under magnetic stirring at room temperature for 10 minutes. After the reaction was completed, it was extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. ) was purified by column chromatography as the eluent to obtain the desired product as a pale yellow solid with a yield of 75%.

[0027] Its NMR data are as follows:

[0028] 1 H NMR (500 MHz, CDCl 3 ): d = 7.95 (1H, d, J = 1.0 Hz), 7.83 (1H, d, J = 1.0 Hz), 7.62 (2H, q, J =1.8 Hz), 7.32 (2H, d, J = 8.0 Hz), 2.43 (3H, s).

Embodiment 2

[0029] Example 2: Synthesis of 1-o-tolyl-1 hydrogen-1,2,3-triazole

[0030]

[0031] Dimethyl sulfoxide (2.5 mL), m-tolyl azide (0.3 mmol), and sodium acetylide (1.2 mmol) were added to the reactor, and the reaction was performed under magnetic stirring at room temperature for 15 minutes. After the reaction was completed, it was extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The crude product was prepared with ethyl acetate / petroleum ether (1:10-1: The volume ratio of 5) is the eluent and is purified by column chromatography to obtain the desired product, which is a light yellow liquid with a yield of 56%.

[0032] Its NMR data are as follows:

[0033] 1 H NMR (500 MHz, CDCl 3 ): d = 7.85 (1H, s), 7. 78 (1H, s), 7.73-7.33 (4H, m), 2.20 (3H, s).

Embodiment 3

[0034] Example 3: Synthesis of 1-p-fluorophenyl-1,2,3-triazole

[0035]

[0036] Dimethyl sulfoxide (1 mL), p-fluorophenyl azide (0.3 mmol), and sodium acetylide (1.5 mmol) were added to the reactor, and the reaction was performed under magnetic stirring at room temperature for 5 minutes. After the reaction was completed, it was extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The crude product was prepared with ethyl acetate / petroleum ether (1:5-1: 3 volume ratio) as the eluent and purified by column chromatography to obtain the desired product as a white solid with a yield of 68%.

[0037] Its NMR data are as follows:

[0038] 1 H NMR (500 MHz, CDCl 3 ): d = 7.95 (1H, d, J = 1.0 Hz), 7.85 (1H, d, J = 1.0 Hz), 7.73 (2H, q, J = 4.6 Hz), 7.24 (2H, q, J = 8.1 Hz).

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Abstract

The invention belongs to technical field of pharmaceuticals and organic synthesis intermediates, particularly relates to a method for synthesizing 1-substituted-1, 2, 3-triazole from sodium acetylide. The specific procedure comprises the following steps: adding dimethyl sulfoxide (DMSO), organic azide and sodium acetylide into a reactor, reacting at room temperature under magnetic stirring for 1-30 min, diluting reaction system with water after reaction, performing extraction with ethyl acetate, washing the organic layer with saturated saline and drying with anhydrous sodium sulfate, evaporating out solvent under reduced pressure to obtain crude product, and purifying with column chromatography with ethyl acetate/petroleum ether as eluent to obtain product, wherein the molar ratio of sodium acetylide to organic azide is (3.5-15):1, the molar ratio of DMSO to organic azide is (20-500):1, and the volume ratio of ethyl acetate to petroleum ether in the eluent is 1:20-4:1. The obtained compound contains 1, 2, 3-triazole structure unit with physiological activity, and can be used as organic synthesis intermediate and for synthesis and modification of pharmaceuticals. The invention also provides a novel and efficient synthesis method for drug screening.

Description

technical field [0001] The invention belongs to the technical field of organic and pharmaceutical synthesis, and in particular relates to a method for synthesizing 1-substituted-1,2,3-triazole by using sodium acetylide. Background technique [0002] Triazole heterocyclic compounds have a wide range of biological activities and have broad application prospects in the fields of medicine, agriculture and materials, and have always been valued by medicinal chemists and biochemists. Among them, 1,2,3-triazole compounds have been gradually developed in recent years, and have significant effects on antibacterial, bactericidal, immune, treatment of tumors, arthritis, rickets, neurotic disorders, etc. (Michael J. G , et al. J. Med. Chem., 2000, 43 , 953-970). [0003] 1,2,3-triazole compounds are an important class of heterocyclic compounds (Alvarez R, et al. J. Med. Chem. , 1994, 37 , 4185-4194), the five-membered heterocyclic ring in the compound has lower toxicity than imida...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06
Inventor 匡春香江玉波
Owner TONGJI UNIV
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