Method for constructing N-2-aryl-substituted-1,2,3-triazole

A technology of triazoles and aryl diazonium salts, applied in steroids, organic chemistry and other directions, can solve the problems of narrow substrate application range, high degree of operational danger, difficult control of selectivity, etc., and achieves good adaptability, Wide adaptability and simple operation

Active Publication Date: 2017-11-24
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its traditional synthetic method is based on the arylation reaction of 1,2,3-triazole (M.Taillefer, N.Xia, A.Ouali, Angew.Chem.Int.Ed.2007,46,934; Angew.Chem.2007 , 119, 952; Y. Liu, W. Yan, Y. Chen, J. L. Petersen, X. Shi, Org. Lett. 2008, 10, 5389; X. Wang, L. Zhang, H. Lee, N. Haddad, D. Krishnamurthy, C.H. Senanayake, Org. Lett. 2009, 11, 5026; S. Ueda, M. Su, S. L. Buchwald, Angew. Chem. Int. Ed. 2011, 50, 8944; Angew. Chem. 2011, 123, 9106) , this type of method not only has the problem of difficult control of selectivity (N1 arylation or N2 arylation), but also needs to use unstable, explosive and dangerous azides as raw materials to synthesize the corresponding 1,2,3- Triazole
The disadvantages of long reaction steps, high operational risk, and narrow scope of substrates have seriously delayed the application and development of N-2-aryl-substituted-1,2,3-triazole compounds in the field of chemical and pharmaceutical materials.

Method used

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  • Method for constructing N-2-aryl-substituted-1,2,3-triazole
  • Method for constructing N-2-aryl-substituted-1,2,3-triazole

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Experimental program
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Effect test

Embodiment 1

[0026] In a 25 ml reaction flask equipped with a reflux condenser, add 0.02 mmol of cuprous chloride, 0.2 mmol of acetophenone oxime ester, 0.2 mmol of p-methoxyphenyldiazotetrafluoroborate, 0.4 mmol Mole of lithium carbonate, 4 ml of toluene, the reaction system was stirred at 70°C for 24 hours, then stopped heating and stirring, and cooled to room temperature. Add water, extract the reaction solution with ethyl acetate, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The column chromatography eluent used is petroleum ether:ethyl acetate with a volume ratio of 1000:1 ester mixed solvent to obtain the product with a yield of 66%.

Embodiment 2

[0028] In a 25 ml reaction flask equipped with a reflux condenser, add 0.02 mmol of cuprous chloride, 0.2 mmol of acetophenone oxime ester, 0.2 mmol of p-methoxyphenyldiazotetrafluoroborate, 0.4 mmol moles of lithium carbonate, 4 ml of toluene, and the reaction system was stirred at 80°C for 24 hours, stopped heating and stirring, and cooled to room temperature. Add water, extract the reaction solution with ethyl acetate, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The column chromatography eluent used is petroleum ether:ethyl acetate with a volume ratio of 1000:1 ester mixed solvent to obtain the product with a yield of 76%.

Embodiment 3

[0030]In a 25 ml reaction flask equipped with a reflux condenser, add 0.02 mmol of cuprous chloride, 0.2 mmol of acetophenone oxime ester, 0.4 mmol of p-methoxyphenyldiazotetrafluoroborate, 0.4 mmol mol of lithium carbonate, 4 ml of toluene, and the reaction system was stirred at 90°C for 12 hours, stopped heating and stirring, and cooled to room temperature. Add water, extract the reaction solution with ethyl acetate, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The column chromatography eluent used is petroleum ether:ethyl acetate with a volume ratio of 1000:1 ester mixed solvent to obtain the product with a yield of 83%.

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Abstract

The invention discloses a method for constructing N-2-aryl-substituted-1,2,3-triazole and belongs to the field of synthesis of pharmaceutical and chemical materials. The method comprises steps as follows: ketoxime ester, aryl diazonium salt, alkali, a copper salt catalyst and a solvent are added to a reactor and are stirred and react for 12-24 h at the temperature of 70-90 DEG C, a product is cooled to the room temperature after the reaction, water and ethyl acetate are added for extraction of a reaction liquid, the solvent is removed through reduced-pressure evaporation, a crude product is obtained and subjected to column chromatography purification, and a N-2-aryl-substituted-1,2,3-triazole compound is obtained. According to the method, the used raw materials are non-toxic, air-stable, cheap and available, and unstable, easily explosive and dangerous azides are not used; the N-2-aryl-substituted-1,2,3-triazole compound is high in reaction selectivity, good in functional group adaptability, wide in substrate adaption range and high in product yield. The synthesis method is simple to operate and safe, adopts mild reaction conditions, is insensitive to water and air and has good industrial application prospect, and enlarged production to gram scale can be realized.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical and chemical materials, and in particular relates to a method for constructing N-2-aryl substituted-1,2,3-triazole. Background technique [0002] N-2-aryl substituted-1,2,3-triazole compounds widely exist in bioluminescent probes (W.Yan, Q.Wang, Q.Lin, M.Li, J.L.Petersen, X.Shi, Chem .Eur.J.2011,17,5011; V.S.Padalkar, S.K.Lanke, S.B.Chemate, N.Sekar, J.Fluoresc.2015,25,985), photocatalyst (R.Cai, W.Yan, M.G.Bologna, K.Silva , Z.Ma, H.O Finklea, J.L.Petersen, M.Li, X.Shi, Org.Chem.Front.2015, 2, 141) and bioactive molecules (Z.J.Jia, C.Venkataramani, W.Huang, M.Mehrotra, Y .Song, Q.Xu, S.M.Bauer, A.Pandey, WO2009136905, 2009; C.D.Cox, M.J.Breslin, D.B.Whitman, J.D.Schreier, G.B.McGaughey, M.J.Bogusky, A.J.Roecker, S.P.Mercer, R.A.Bednar, W.Lemaire, J.G. Bruno, D.R. Reiss, C. Meacham Harrell, K.L. Murphy, S.L. Garson, S.M. Doran, T. Prueksaritanont, W.B. Anderson, C. Tang, S. R...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06C07D249/16C07J71/00
CPCC07D249/06C07D249/16C07J71/0052
Inventor 江焕峰竺传乐
Owner SOUTH CHINA UNIV OF TECH
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