One-pot method for synthesizing 4-acetyl-1,2,3-triazole compounds

A technology of a triazole compound and a synthesis method, which is applied in directions such as organic chemistry, can solve the problems of harsh reaction conditions, difficult synthesis, expensive catalysts, etc., and achieves the effects of mild reaction conditions, a wide range of substrates, and low-cost catalysts

Active Publication Date: 2020-05-22
WUHAN INSTITUTE OF TECHNOLOGY
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AI Technical Summary

Problems solved by technology

Therefore, it is greatly limited in the application of synthesizing 1,4-disubstituted-1,2,3-triazole compounds
[0005] Later, with the discovery of the "click" reaction, 4-acetyl substituted triazoles can also be prepared from terminal alkynes and azide compounds containing hydroxyl or carbonyl groups, and then oxidized to obtain the desired product, but this method requires noble metals Catalysis, harsh reaction conditions, low selectivity and low yield
Later, some small molecule-catalyzed methods of preparing 4-acetyltriazole by reacting alkenes and organic azides were also discovered, but because alkenes are easy to polymerize, the yield of the reaction is not very high, and industrialization is limited by conditions.
Recently, there are also many reports on the synthesis of 4-acetyl 1,2,3-triazole by azide-free three-component reaction, but the reaction takes a long time and the reaction conditions are harsh
[0006] In summary, the above methods for synthesizing 4-acetyl-1,2,3-triazole compounds are all difficult to form, long reaction time, high reaction temperature, low yield, few suitable substrates or difficult synthesis, raw material toxicity Disadvantages such as large or poor safety, expensive catalysts, etc.

Method used

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  • One-pot method for synthesizing 4-acetyl-1,2,3-triazole compounds
  • One-pot method for synthesizing 4-acetyl-1,2,3-triazole compounds
  • One-pot method for synthesizing 4-acetyl-1,2,3-triazole compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Synthesis of (N-benzyl-1,2,3-triazole-4-substituted) (phenyl)methanone, the reaction formula is:

[0022]

[0023] The specific steps are: add 0.33mmol acetophenone, 0.50mmol benzyl azide, 0.09mmol Cu(NO 3 ) 2 , 1 mmol K 2 S 2 O 8 , 0.09mmol TMEDA, 3mL DMF, magnetically stirred at 110°C for 5 hours, extracted the reaction solution with ethyl acetate, washed the organic layer with saturated brine, dried over anhydrous sodium sulfate, evaporated the solvent under reduced pressure to obtain crude The product, the crude product was purified by column separation and purification with ethyl acetate / petroleum ether=1:5 (V / V) as the eluent to obtain the desired product, which was a white solid with a yield of 80%.

[0024] The proton nuclear magnetic spectrogram result of gained product is: 1 H NMR (600MHz, CDCl 3 )δ8.46–8.39(m,1H),8.17(s,1H),7.61(m,J=10.8,3.9Hz,1H),7.51(t,J=7.8Hz,1H),7.40(d,J =6.9Hz,1H),7.33(d,J=7.5Hz,1H),5.60(s,1H).

Embodiment 2

[0026] (N-benzyl-1,2,3-triazole-4-substituted) (4-methoxyphenyl) ketone synthesis, the reaction formula is:

[0027]

[0028] The specific steps are: add 0.33mmol 4-methoxyacetophenone, 0.50mmol benzyl azide, 0.09mmol Cu(NO 3 ) 2 , 1 mmol K 2 S 2 O 8 , 0.09mmol TMEDA, 3mL DMF, magnetically stirred at 110°C for 5 hours, extracted the reaction solution with ethyl acetate, washed the organic layer with saturated brine, dried over anhydrous sodium sulfate, evaporated the solvent under reduced pressure to obtain crude The product, the crude product was purified by column separation and purification with ethyl acetate / petroleum ether=1:5 (V / V) as the eluent to obtain the desired product, which was a white solid with a yield of 85%.

[0029] The proton nuclear magnetic spectrogram result of gained product is: 1 H NMR (600MHz, CDCl 3 )δ8.34(d, J=8.1Hz, 2H), 8.16(s, 1H), 7.33(m, 7H), 5.59(s, 2H), 3.41(s, 3H).

Embodiment 3

[0031] (N-benzyl-1,2,3-triazole-4-substituted) (4-fluorophenyl) ketone synthesis, the reaction formula is:

[0032]

[0033] The specific steps are: add 0.33mmol 4-fluoroacetophenone, 0.50mmol benzyl azide, 0.09mmol Cu(NO 3 ) 2 , 1 mmol K 2 S 2 O 8 , 0.09mmol TMEDA, 3mL DMF, magnetically stirred at 110°C for 5 hours, extracted the reaction solution with ethyl acetate, washed the organic layer with saturated brine, dried over anhydrous sodium sulfate, evaporated the solvent under reduced pressure to obtain the crude The product, the crude product was purified by column separation and purification with ethyl acetate / petroleum ether=1:5 (V / V) as the eluent to obtain the desired product, which was a white solid with a yield of 87%.

[0034] The proton nuclear magnetic spectrogram result of gained product is: 1 H NMR (600MHz, CDCl 3 )δ8.53(m,2H),8.18(s,1H),7.45–7.31(m,5H),7.21–7.14(m,2H),5.61(s,2H).

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Abstract

The invention relates to a method of synthesizing 4-acetyl-1,2,3-triazole compounds by using a one-pot method, and belongs to the technical fields of organic chemistry and medicine synthesis. A copper salt is used as a catalyst, a ligand and an oxidizing agent are employed, and in a DMF solvent, a reaction of an aryl methanone and an organic azide is performed in the solvent by a one-pot method. The method provided by the invention has beneficial effects that the method uses the cheap and easily-available copper salt as the catalyst; the aryl methanone and the organic azide are reacted by a one-pot method; the reaction conditions are mild; the yield is high; the raw materials are easy to acquire; and the 4-acetyl-1,2,3-triazole compounds are synthesized conveniently and effectively. Compared with methods in the prior art, the method provided by the invention has mild reaction conditions, short reaction time, good safety, simple and convenient operation, a wide substrate range and high reaction efficiency, employs a cheap catalyst, and is a method which has potential application values.

Description

technical field [0001] The invention relates to a method for synthesizing 4-acetyl-1,2,3-triazole compounds in one pot, and belongs to the technical field of organic and pharmaceutical synthesis. [0002] technical background [0003] 1,2,3-Triazole compounds are a class of nitrogen-containing heterocyclic compounds with important physiological activities, widely used in preservatives, pesticides, optical materials, dyes, HIV-1 inhibitors, antibiotics, selective β 3 - Adrenal antagonists, antivirals and anticonvulsants. Activity assays showed that 4-acetyl-1,2,3-triazole compounds can act as orally bioavailable transcriptional function inhibitors of human estrogen-related receptor α. Recent literature reports that some 4-acetyl-1,2,3-triazole compounds can also be used as channel blockers to treat heart tremors, so 4-acetyl-1,2,3-triazole compounds It can be used as a treatment for various major human diseases such as cancer and heart disease, and has a broad market prospec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/04C07D409/06C07D249/06
CPCC07D249/04C07D249/06C07D409/06
Inventor 陈云峰刘艺聂刚
Owner WUHAN INSTITUTE OF TECHNOLOGY
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