Synthesis method of NH-1,2,3-triazole compound

A synthesis method and acid catalyst technology, applied in organic chemistry and other fields, can solve the problems of high toxicity of raw materials, high reaction temperature, and long reaction time, and achieve the effects of low catalyst, high reaction efficiency, and short reaction time

Active Publication Date: 2016-06-15
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In summary, the above methods for synthesizing NH-1,2,3-triazole compounds are all difficult to generate, long reaction time, high reaction temperature, low yield, few suitable substrates or difficult synthesis, high toxicity of raw materials or safety Poor performance, expensive catalyst and other disadvantages

Method used

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  • Synthesis method of NH-1,2,3-triazole compound
  • Synthesis method of NH-1,2,3-triazole compound
  • Synthesis method of NH-1,2,3-triazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Synthesis of 4-phenyl-2H-1,2,3-triazole:

[0023] The reaction formula is:

[0024]

[0025] The specific steps are: add 0.33mmol benzaldehyde, 0.50mmol nitromethane, 0.39mmol sodium azide, 0.03mmol AlCl to a 50mL round bottom flask 3 , 2mLDMSO, magnetically stirred at 80°C for 12 hours, then extracted the reaction solution with ethyl acetate, washed the organic layer with saturated brine, dried over anhydrous sodium sulfate, and evaporated the solvent under reduced pressure to obtain the crude product. Ethyl acetate / petroleum ether=1:5 (V / V) was used as the eluent for column separation and purification to obtain the desired product, which was a white solid with a yield of 94%.

[0026] The proton nuclear magnetic spectrogram result of gained product is: 1 HNMR (600MHz, DMSO-d 6 ): δ8.32(s,1H),7.84(d,J=7.4Hz,2H),7.43(t,J=7.7Hz,2H),7.33(t,J=7.4Hz,1H).

Embodiment 2

[0028] Synthesis of 4-phenyl-2H-1,2,3-triazole:

[0029] The reaction formula is:

[0030]

[0031] The specific steps are: add 0.33mmol benzaldehyde, 0.50mmol nitromethane, 0.39mmol sodium azide, 0.03mmol ZnCl to a 50mL round bottom flask 2 , 2mLDMSO, magnetically stirred at 80°C for 12 hours, then extracted the reaction solution with ethyl acetate, washed the organic layer with saturated brine, dried over anhydrous sodium sulfate, and evaporated the solvent under reduced pressure to obtain the crude product. Ethyl acetate / petroleum ether=1:5 (V / V) was used as the eluent for column separation and purification to obtain the desired product, which was a white solid with a yield of 75%.

[0032] The proton nuclear magnetic spectrogram result of gained product is: 1 HNMR (600MHz, DMSO-d 6 ): δ8.32(s,1H),7.84(d,J=7.4Hz,2H),7.43(t,J=7.7Hz,2H),7.33(t,J=7.4Hz,1H).

Embodiment 3

[0034] Synthesis of 4-phenyl-2H-1,2,3-triazole:

[0035] The reaction formula is:

[0036]

[0037] The specific steps are: add 0.33mmol benzaldehyde, 0.50mmol nitromethane, 0.39mmol sodium azide, 0.03mmol FeCl to a 50mL round bottom flask 3, 2mLDMSO, magnetically stirred and reacted at 80°C for 12 hours, then extracted the reaction solution with ethyl acetate, washed the organic layer with saturated brine, dried over anhydrous sodium sulfate, and evaporated the solvent under reduced pressure to obtain the crude product. Ethyl acetate / petroleum ether=1:5 (V / V) was used as the eluent for column separation and purification to obtain the desired product, which was a white solid with a yield of 70%.

[0038] The proton nuclear magnetic spectrogram result of gained product is: 1 HNMR (600MHz, DMSO-d 6 ): δ8.32(s,1H),7.84(d,J=7.4Hz,2H),7.43(t,J=7.7Hz,2H),7.33(t,J=7.4Hz,1H).

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Abstract

The invention relates to a synthesis method of an NH-1,2,3-triazole compound and belongs to the technical field of organic and drug synthesis. In the presence of a Lewis acid catalyst, the NH-1,2,3-triazole compound is prepared from aromatic aldehyde, nitro-hydrocarbon and sodium azide by adopting a one-pot process. The synthesis method of the NH-1,2,3-triazole compound has the beneficial effects that available Lewis acids such as AlCl3 are taken as the catalyst, one-pot reaction is carried out on aromatic aldehyde, a nitro-hydrocarbon compound containing alpha hydrogen (wherein hydrocarbon is C1-C6 alkyls, C1-C6 alkoxys or ethyl formate) and sodium azide, reaction conditions are mild, yield is high, raw materials are available, the NH-1,2,3-triazole compound is conveniently and effectively synthesized, and compared with an existing method, the synthesis method provided by the invention is mild in reaction conditions, short in reaction time, good in safety, simple in operation, wide in substrate range and high in reaction efficiency and adopts a cheap catalyst, so that the synthesis method provided by the invention has potential application value.

Description

technical field [0001] The invention relates to a method for synthesizing NH-1,2,3-triazole compounds, belonging to the technical field of organic and pharmaceutical synthesis. technical background [0002] 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 testing shows that 4-aryl-NH-1,2,3-triazole compounds can be used as human methionine aminopeptidase inhibitors. Recent literature reports that some 4-aryl-NH-1,2,3-triazole compounds also have indoleamine 2,3-dioxygenase inhibitory activity and are potential IDO inhibitors, so NH-1, 2,3-triazole compounds can be used to treat various major human diseases such as cancer, Alzheimer's disease, and cataract, and have broad market prospects. [0003] The early 1,3-dipolar Huisge...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06C07D401/04C07D405/04
CPCC07D249/06C07D401/04C07D405/04
Inventor 陈云峰胡钦铨刘艺邓小聪
Owner WUHAN INSTITUTE OF TECHNOLOGY
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