研究论文

铜催化的2H-1,2,3-三氮唑的绿色制备

  • 毕晶晶 ,
  • 孙潇潇 ,
  • 高松 ,
  • 陈长坡 ,
  • 张贵生
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  • 河南师范大学化学化工学院 绿色化学介质与反应教育部重点实验室 精细化学品绿色制造协同创新中心 河南省有机功能分子与药物创新重点实验室 河南新乡 453007

收稿日期: 2021-01-06

  修回日期: 2021-03-22

  网络出版日期: 2021-04-16

基金资助

国家自然科学基金(21702051); 河南省博士后科学基金(001802033); 河南省科技攻关(212102311022); 河南师范大学青年科学基金(2016QK10)

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)

摘要

报道了4-取代-1-磺酰基-1,2,3-三氮唑在绿色溶剂中的催化水解反应, 以1 mol%硫酸铜作为催化剂, 在水/ PEG-400混合溶剂中以较高的收率高效合成了4-取代-2H-1,2,3-三氮唑. 该方法为制备2H-1,2,3-三氮唑类化合物提供了一种绿色、简单、有效的方法. 此外, 还用一锅法对2H-1,2,3-三氮唑进行了溴化、芳基化、烷基化的探索, 效果良好.

本文引用格式

毕晶晶 , 孙潇潇 , 高松 , 陈长坡 , 张贵生 . 铜催化的2H-1,2,3-三氮唑的绿色制备[J]. 有机化学, 2021 , 41(7) : 2760 -2766 . DOI: 10.6023/cjoc202101010

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.

参考文献

[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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