铜催化的2H-1,2,3-三氮唑的绿色制备

doi:10.6023/cjoc202101010

有机化学 ›› 2021, Vol. 41 ›› Issue (7): 2760-2766.DOI: 10.6023/cjoc202101010 上一篇下一篇

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^*()

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 发布日期:2021-04-16
通讯作者: 毕晶晶, 张贵生
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()

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

Received:2021-01-06 Revised:2021-03-22 Published:2021-04-16
Contact: Jingjing Bi, Guisheng Zhang
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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摘要/Abstract

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.

关键词: 2H-1,2,3-三氮唑, 硫酸铜, 三唑衍生物, 绿色溶剂

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

引用此文

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.

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.

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Entry	Acid (equiv.)	Solvent	Time/h	T/℃	2a, Yield^b/%
1	TsOH (0.01)	H₂O	4	80	40
2	BF₃•Et₂O (1.0)	DCE	0.5	80	Trace
3	BF₃•Et₂O (2.0)	DCE	0.5	80	Trace
4	BF₃•Et₂O (4.0)	DCE	0.5	80	Trace
5	BF₃•Et₂O (6.0)	DCE	0.5	80	47
6	CuSO₄ (0.01)	H₂O	0.5	80	90
7	ZnSO₄ (0.01)	H₂O	0.5	80	38
8	CuSO₄ (0.01)	H₂O	6	40	Trace
9	CuSO₄ (0.01)	H₂O	6	60	20^c
10	CuSO₄(0.01)	H₂O/PEG-400 (V∶V=4∶1)	15	60	79^e
11	CuSO₄(0.01)	H₂O/PEG-400 (V∶V=10∶1)	24	60	83
12	CuSO₄(0.01)	H₂O/PEG-400 (V∶V=10∶1)	4	80	96
13	ZnSO₄ (0.01)	H₂O/PEG-400 (V∶V=10∶1)	5	80	95

Entry	Acid (equiv.)	Solvent	Time/h	T/℃	2a, Yield^b/%
1	TsOH (0.01)	H₂O	4	80	40
2	BF₃•Et₂O (1.0)	DCE	0.5	80	Trace
3	BF₃•Et₂O (2.0)	DCE	0.5	80	Trace
4	BF₃•Et₂O (4.0)	DCE	0.5	80	Trace
5	BF₃•Et₂O (6.0)	DCE	0.5	80	47
6	CuSO₄ (0.01)	H₂O	0.5	80	90
7	ZnSO₄ (0.01)	H₂O	0.5	80	38
8	CuSO₄ (0.01)	H₂O	6	40	Trace
9	CuSO₄ (0.01)	H₂O	6	60	20^c
10	CuSO₄(0.01)	H₂O/PEG-400 (V∶V=4∶1)	15	60	79^e
11	CuSO₄(0.01)	H₂O/PEG-400 (V∶V=10∶1)	24	60	83
12	CuSO₄(0.01)	H₂O/PEG-400 (V∶V=10∶1)	4	80	96
13	ZnSO₄ (0.01)	H₂O/PEG-400 (V∶V=10∶1)	5	80	95

铜催化的2H-1,2,3-三氮唑的绿色制备

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

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