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Method for preparing 4-aryl-NH-1,2,3-triazole by aid of aldehyde and sodium bisulfite adduct

A technology of aryl and compound, applied in the direction of organic chemistry, can solve problems such as differences in reactivity, achieve simple operation, easy industrial production, and improve production efficiency

Active Publication Date: 2016-11-23
HAINAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

On the other hand, compared with the aldehyde, the adduct has certain changes and differences in reactivity

Method used

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  • Method for preparing 4-aryl-NH-1,2,3-triazole by aid of aldehyde and sodium bisulfite adduct
  • Method for preparing 4-aryl-NH-1,2,3-triazole by aid of aldehyde and sodium bisulfite adduct
  • Method for preparing 4-aryl-NH-1,2,3-triazole by aid of aldehyde and sodium bisulfite adduct

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Synthesis of 4-phenyl-NH-1,2,3-triazole:

[0017] The reaction formula is:

[0018]

[0019] Specific steps: Add 1 mmol of benzaldehyde sodium bisulfite adduct, 2.0 mmol of sodium azide, 4.0 mmol of nitromethane and 1.0 mL of dimethyl sulfoxide into a 10 mL round bottom flask, and heat at 120°C for 4 hours. After the reaction, the reaction system was cooled to room temperature, the reaction solution was all transferred to a separatory funnel, 30 mL of ethyl acetate, 30 mL of water and 10 mL of saturated ammonium chloride aqueous solution were added to extract and separate the liquid, and the organic phase was washed 3 times with water ( 10mL * 3), washed once with saturated brine (10mL), and dried over anhydrous sodium sulfate. The desiccant was filtered off, the filtrate was removed from the solvent under reduced pressure, and the silica gel column chromatography was performed. The eluent was petroleum ether / ethyl acetate (v: v = 4:1). Fractions were collected to ...

Embodiment 2

[0021] Synthesis of 4-phenyl-NH-1,2,3-triazole:

[0022] The reaction formula is:

[0023]

[0024] Specific steps: Add 1.0 mmol benzaldehyde sodium bisulfite adduct, 1.0 mmol sodium azide, 1.0 mmol NaHSO to a 10 mL round bottom flask 3 and 3 mL of dimethyl sulfoxide, the reaction system was replaced with nitrogen, and a N,N dimethylformamide (DMF) solution containing 1.0 mmol of nitromethane was added dropwise at 60°C. After the dropwise addition, continued heating for 10 hours. Other operations are the same as in Example 1, and the yield is 42%.

Embodiment 3

[0026] Synthesis of 4-phenyl-NH-1,2,3-triazole:

[0027] The reaction formula is:

[0028]

[0029] Specific steps: Add 1.0 mmol benzaldehyde, 2.0 mmol sodium azide, 1.0 mmol Na 2 SO 3 and 3 mL of N-methylpyrrolidone (NMP), add dropwise an NMP solution (2 mL) containing 4.0 mmol of nitromethane at 120°C, and continue heating for 5 hours after the addition is complete. Other operations are the same as in Example 1, and the yield is 45%.

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Abstract

The invention relates to a method for preparing 4-aryl-NH-1,2,3-triazole by the aid of aldehyde and sodium bisulfite adduct. The method is characterized by comprising steps as follows: the aldehyde and sodium bisulfite adduct, a nitrocompound, sodium azide, a solvent and an additive react at the temperature of 60-150 DEG C for 1-10 h with a one-pot method, after the reaction ends, aftertreament is performed, and 4-aryl-NH-1,2,3-triazole can be prepared. The cheap and easy-to-obtain aldehyde and sodium bisulfite adduct, nitrocompound and sodium azide are taken as raw materials, and 4-aryl-NH-1,2,3-triazole compounds can be conveniently prepared from the three components. Compared with existing methods, the method has the advantages that the raw materials are low in cost and simple and easy to obtain, the operation is convenient, and the reaction efficiency is high.

Description

technical field [0001] The invention relates to a synthesis method of 1,2,3-triazole, in particular to a synthesis method of 4-aryl-NH-1,2,3-triazole, and belongs to the fields of organic synthesis, drug synthesis and organic materials. Background technique [0002] 1,2,3-triazole is a five-membered heterocyclic compound containing three nitrogen atoms. At present, 1,2,3-triazole compounds are used in many fields, such as antibacterial, antiviral, antitumor, anti-HIV, anti-epileptic, etc. in medicine, and can also be used in pesticides, dyes and other fields. 4-aryl-NH-1,2,3-triazole is a special class among many triazole compounds. Experimental studies have shown that NH-1,2,3-triazole has special biological activity. Many papers have studied the inhibitory effect of NH-1,2,3-triazoles on indoleamine-2,3-dioxygenase (IDO) in detail. Meanwhile, NH-1,2,3-triazole has inhibitory activity on methionine peptidase (hMetAP2). In vitro experiments show that 4-aryl-NH-1,2,3-triaz...

Claims

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Application Information

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IPC IPC(8): C07D249/06C07D401/04C07D409/04
CPCC07D249/06C07D401/04C07D409/04
Inventor 陈昱学何文英宋鑫明吴禄勇黄青兰
Owner HAINAN NORMAL UNIV
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