Method for synthesizing 1-substituted-1,2,3-tolyltriazole

A synthetic method, triazole technology, applied in the field of organic and pharmaceutical synthesis, can solve problems such as no effective synthetic route, and achieve the effect of high yield, easy industrialization, novel and effective synthetic method

Inactive Publication Date: 2010-08-04
TONGJI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For the synthesis of 1-substituted-1,2,3-triazoles, there is still no effective synthetic approach so far, and t

Method used

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  • Method for synthesizing 1-substituted-1,2,3-tolyltriazole
  • Method for synthesizing 1-substituted-1,2,3-tolyltriazole
  • Method for synthesizing 1-substituted-1,2,3-tolyltriazole

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1: the synthesis of 1-p-tolyl-1,2,3-triazole

[0022]

[0023] Add cuprous iodide (0.07mmol), sodium ascorbate (0.14mmol), p-tolyl azide (0.4mmol), propiolic acid (0.57mmol) and DMF 2mL to the reactor, and react with magnetic stirring at room temperature for 16 hours, 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 at a volume ratio of ethyl acetate / petroleum ether=1:2 The eluent was purified by column chromatography to obtain the desired product as a light yellow solid with a yield of 87%.

[0024] Its NMR data are as follows:

[0025] 1 H NMR (500MHz, CDCl 3 ): δ = 7.95 (1H, d, J = 1.0Hz), 7.83 (1H, d, J = 1.0Hz), 7.62 (2H, q, J = 1.8Hz), 7.32 (2H, d, J = 8.0Hz ), 2.43 (3H, s).

Embodiment 2

[0026] Embodiment 2: Synthesis of 1-p-fluorophenyl-1,2,3-triazole

[0027]

[0028] Add cuprous iodide (0.07mmol), sodium ascorbate (0.14mmol), p-fluorophenyl azide (0.37mmol), propiolic acid (0.55mmol), triethylamine (0.19mmol) and DMF 2mL to the reactor , and reacted with magnetic stirring at 60 °C for 3 hours. 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 : volume ratio of 3) was the eluent and purified by column chromatography to obtain the desired product as a white solid with a yield of 90%.

[0029] Its NMR data are as follows:

[0030] 1 H NMR (500MHz, CDCl 3 ): δ = 7.95 (1H, d, J = 1.0Hz), 7.85 (1H, d, J = 1.0Hz), 7.73 (2H, q, J = 4.6Hz), 7.24 (2H, q, J = 8.1Hz ).

Embodiment 3

[0031] Example 3: Synthesis of 1-p-methoxyphenyl-1,2,3-triazole

[0032]

[0033] Add cuprous iodide (0.02mmol), sodium ascorbate (0..04mmol), p-methoxyphenyl azide (0.34mmol), propiolic acid (0.50mmol), DBU (0.17mmol) and DMF 2mL, magnetically stirred at 80°C for 5 hours. 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 : 2 volume ratio) as the eluent and purified by column chromatography to obtain the desired product as a yellow solid with a yield of 94%.

[0034] Its NMR data are as follows:

[0035] 1 H NMR (500MHz, CDCl 3 ): δ = 7.91 (1H, d, J = 0.8Hz), 7.83 (1H, d, J = 0.8Hz), 7.64 (2H, q, J = 2.2Hz), 7.03 (2H, q, J = 2.2Hz ), 3.87 (3H, s).

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Abstract

The invention belongs to the technical field of organics and medicinal synthesis and particularly relates to a method for synthesizing 1-substituted-1,2,3-tolyltriazole, which comprises the following steps: adding cuprous halide or copper sulfate serving as a catalyst, sodium ascorbate, an organic trinitride compound and propiolic acid into a solvent, magnetically stirring the solution to perform reactions at the temperature of between room temperature and 200 DEG C below zero for 0.5 hour to 3 days, extracting the resulting product by using ethyl acetate or dichloromethane after the reactions are finished, washing an organic layer with saturated salt solution, drying the organic layer with anhydrous sodium sulfate, removing the solvent to obtain a coarse product, and subjecting the coarse product to column chromatographic separation and purification by using a mixture of ethyl acetate and petroleum ether as leacheate to obtain the required product, wherein the molar ratio of the propiolic acid to the organic trinitride compound is 1-2.0:1; the molar ratio of the cuprous halide or copper sulfate serving as the catalyst to the organic trinitride compound is 0.1-0.3:1; and the molar ratio of the sodium ascorbateto the organic trinitride compound is 0.2-0.4:1. The compound of the invention contains 1,2,3-tolyltriazole structural units with physiological activity and can be used for synthesizing and modifying organically synthesized intermediates and medicaments. Meanwhile, a novel and effective synthesis method is provided for medicament screening.

Description

technical field [0001] The invention belongs to the technical field of organic and pharmaceutical synthesis, and in particular relates to a synthesis method of 1-substituted-1,2,3-triazole. 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. Wherein 1,2,3-triazole compounds have been developed gradually in recent years, and have significant effects on antibacterial, bactericidal, immune, treatment of tumors, arthritis, rickets, nervous disorders, etc. (Michael J.G, et al. al. J. Med. Chem., 2000, 43, 953-970). [0003] 1,2,3-triazole compounds are a class of important heterocyclic compounds (Alvarez R, et al.J. Med.Chem., 1994, 37, 4185-4194), and the five-membered heterocyclic ring in the compound acts as a drug effect The group has lower toxicity than imidazole, a...

Claims

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Application Information

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IPC IPC(8): C07D417/04C07D249/06
Inventor 匡春香许梅王卓程学智
Owner TONGJI UNIV
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