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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 7: 2760 - 2766

DOI: https://doi.org/10.6023/cjoc202101010

ARTICLES

Copper Catalyzed Synthesis of 2H-1,2,3-Triazoles in Green Solvent

  • Jingjing Bi ,
  • Xiaoxiao Sun ,
  • Song Gao ,
  • Changpo Chen ,
  • Guisheng Zhang
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  • Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Henan Key laboratory of Organic Functional Molecule and Drug Innovation, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
* Corresponding authors. E-mail: ;

Received date: 2021-01-06

  Revised date: 2021-03-22

  Online published: 2021-04-16

Supported by

National Natural Science Foundation of China(21702051); Postdoctoral Science Foundation of Henan Province(001802033); Henan Science and Technology Program(212102311022); Henan Normal University Science Foundation for Young Scholars(2016QK10)

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Abstract

The hydrolysis of 4-substituted 1-sulfonyl-1,2,3-triazoles induced by a catalytic amount of copper sulfate in the green solvent of H2O/PEG-400 was reported, providing a wide range of 4-substituted-2H-1,2,3-triazoles in excellent yields. The approach provides a green, simple and effective method for the preparation of 2H-1,2,3-triazole compounds. Bromination, arylation, and alkylation on 2H-1,2,3-triazoles by the one-pot method were also explored.

Key words： 2H-1,2,3-triazole; copper sulfate; triazole derivative; green solvent

Cite this article

Jingjing Bi , Xiaoxiao Sun , Song Gao , Changpo Chen , Guisheng Zhang . Copper Catalyzed Synthesis of 2H-1,2,3-Triazoles in Green Solvent[J]. Chinese Journal of Organic Chemistry, 2021 , 41(7) : 2760 -2766 . DOI: 10.6023/cjoc202101010

References

[1]
(a) Liu, Q.; Lü, Y.; Bao, P.; Yue, H.; Wei, W. Chin. J. Org. Chem. 2020, 40,4015 (in Chinese).
[1]
( 刘启顺, 吕玉芬, 鲍鹏丽, 岳会兰, 魏伟, 有机化学, 2020, 40,4015.)
[1]
(b) Zhang, F.; Peng, X.; Ma, J. Chin. J. Org. Chem. 2019, 39,109 (in Chinese).
[1]
( 张发光, 彭星, 马军安, 有机化学, 2019, 39,109.)
[1]
(c) Dong L.; Wang S.; Zhang X.; Cheng J.; Yuan Y. Chem. J. Chin. Univ. 2019, 40,927 (in Chinese).
[1]
( 董丽蓉, 王思雨, 张小媚, 成佳佳, 袁耀锋, 高等学校化学学报, 2019, 40,927.)
[1]
(d) Liu, Z.; Hao, W.; Gao, W.; Zhu, G.; Li, X.; Tong, L.; Tang, B. Sci. China Chem. 2019, 62,1001.
[2]
(a) Yao, Y.; Ren, C.; Chen, L.; Zhong, L.; Xu, T.; Tan, C. Chin. J. Org. Chem. 2021, 41,2055 (in Chinese).
[2]
( 姚阳意, 任朝丽, 陈丽, 钟良坤, 许天明, 谭成侠, 有机化学, 2021, 41,2055.)
[2]
(b) Sheng, C.; Zhang, W. Curr. Med. Chem. 2011; 18,733.
[2]
(c) Wang, C.; Zhou, F.; Zhou, J. Chin. J. Org. Chem. 2020, 40,3065 (in Chinese).
[2]
( 王才, 周锋, 周剑, 有机化学, 2020, 40,3065.)
[2]
(d) Zheng, B.; Cheng, S.; Dong, H.; Zhu, J.; Han, Y.; Yang, L.; Hu, J. Acta Chim. Sinica 2020, 78,1089 (in Chinese).
[2]
( 郑斌, 程盛, 董华泽, 朱金苗, 韩钰, 杨亮, 胡进明, 化学学报, 2020, 78,1089.)
[3]
(a) Zhang, L.; Zhao, J.; Wang, Y. Acta Chim. Sinica 2015, 73,1182 (in Chinese).
[3]
( 张丽芳, 赵杰, 王勇, 化学学报, 2015, 73,1182.)
[3]
(b) Gao, C.; Chang, L.; Xu, Z.; Yan,X. -F.; Ding, C.; Zhao, F.; Wu, X.; Feng,L. -S. Eur. J. Med. Chem. 2019, 163,404.
[4]
(a) Bonandi, E.; Christodoulou,M. S.; Fumagalli, G.; Perdicchia, D.; Rastelli, G.; Passarella, D. Drug Discovery Today 2017, 22,1572.
[4]
(b) Cheng W.; Wang W.; Shang H.; Zhang H.; Guo Q.; Chen H.; Zou Z. J. China Pharm. Univ. 2018, 49,56 (in Chinese).
[4]
( 成伟华, 王文倩, 尚海, 张宏武, 郭强, 陈虹, 邹忠梅, 中国药科大学学报, 2018, 49,56.)
[5]
Deng, L.; Cao, X.; Liu, Y.; Wan,J. -P. J. Org. Chem. 2019, 84,14179.
[6]
Zhang, W.; Kuang, C.; Yang, Q. Synthesis. 2010,283.
[7]
Barluenga, J.; Valdés, C.; Beltrán, G.; Escribano, M.; Aznar, F. Angew. Chem. Int. Ed. 2006, 45,6893.
[8]
Quan,X. -J.; Ren,Z. -H., Wang,Y. -Y.; Guan,Z. -H. Org. Lett. 2014, 16,5728.
[9]
Shu, W.; Zhang, X.; Zhang, X.; Li, M.; Wang, A.; Wu, A. J. Org. Chem. 2019, 84,14919.
[10]
Taylor,S. D.; Lohani,C. R. Org. Lett. 2016, 18,4412.
[11]
Gao, Y.; Lam, Y. Org. Lett. 2006, 8,3283.
[12]
Hu, Q.; Liu, Y.; Deng, X.; Li, Y.; Chen, Y. Adv. Synth. Catal. 2016, 358,1689.
[13]
Dong, H.; Zhang, D.; Fang, R.; Du, Q.; Dong, Zh.; Wei, H.; Shi, M.; Wang, F. Synth. Commun. 2018, 48,1227.
[14]
(a) Raushel, J.; Fokin,V. V. Org. Lett. 2010, 12,4952.
[14]
(b) Shao, C.; Wang, X.; Zhang, Q.; Luo, S.; Zhao, J.; Hu, Y. J. Org. Chem. 2011, 76,6832.
[14]
(c) Liu, Y.; Wang, X.; Xu, J.; Zhang, Q.; Zhao, Y.; Hu, Y. Tetrahedron 2011, 67,6294.
[15]
Wang, X.; Sidhu, K.; Zhang, L.; Campbell, S.; Haddad, N.; Reeves,D. C.; Krishnamurthy, D.; Senanayake,C. H. Org. Lett. 2009, 11,5490.
[16]
Liu, Y.; Yan, W.; Chen, Y.; Petersen,J. L.; Shi, X. Org. Lett. 2008, 10,5389.
[17]
(a) Zhang, M.; Zhang, A. J. Heterocycl. Chem. 2012, 49,721.
[17]
(b) Zhang, M.; Wang, Q.; Peng, Y.; Chen, Z.; Wan, C.; Chen, J.; Zhao, Y.; Zhang, R.; Zhang, A. Chem. Commun. 2019, 55,13048.
[18]
Deng, X.; Lei, X.; Nie, G.; Jia, L.; Li, Y.; Chen, Y. J. Org. Chem. 2017, 82,6163.
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