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A kind of method that solvent participates in reaction synthesis 4-acetyl-1,2,3-triazole compound

A triazole compound and acetyl group technology, which is applied in the field of organic and pharmaceutical synthesis, can solve the problems of harsh reaction conditions, difficult synthesis, high reaction temperature, etc., and achieve the effects of mild reaction conditions, wide substrate range and high reaction efficiency

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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  • A kind of method that solvent participates in reaction synthesis 4-acetyl-1,2,3-triazole compound
  • A kind of method that solvent participates in reaction synthesis 4-acetyl-1,2,3-triazole compound
  • A kind of method that solvent participates in reaction synthesis 4-acetyl-1,2,3-triazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Synthesis of (N-benzyl-1,2,3-triazole-4-substituted)(phenyl)methanone:

[0021] 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 DMA, after magnetic stirring at 110°C for 5 hours, the reaction solution 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 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 83%.

[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 DMA, after magnetic stirring at 110°C for 5 hours, the reaction solution 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 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 the product of gained 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 DMA, after magnetic stirring at 110°C for 5 hours, the reaction solution 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 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 the product of gained is: 1H 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 for synthesizing a 4-acetyl-1,2,3-triazole compound through a solvent participating in a reaction. The solvent participating in the reaction provides a carbon source, the solvent is one of DMA, DMSO, TMEDA and DMF-DMA, metal salt is used as a catalyst, the TMEDA is used as a ligand and an oxidant, and a methyl ketone compound and organic azide undergo a one-pot reaction. The cheap and easily available solvent participates in the reaction, the copper salt is used as the catalyst, and the methyl ketone compound and the organic azide undergo the one-pot reaction, so the method has the characteristics of mild reaction conditions, high yield, easily available raw materials, and convenience in effective synthesis of the 4-acetyl-1,2,3-triazole compound; and compared with existing methods, the method disclosed in the invention has the advantages of mild reaction conditions, short reaction time, good safety, simplicity in operation, wide substrate application, high reaction efficiency and cheap catalyst, and is a method having potential application values.

Description

technical field [0001] The invention relates to a method for synthesizing a 4-acetyl-1,2,3-triazole compound by participating in a reaction with a solvent, 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 dis...

Claims

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Application Information

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