Electrochemical Multicomponent Cascade Synthesis of 4-Selenylacylpyrazoles

doi:10.6023/cjoc202503018

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (10): 3807-3815.DOI: 10.6023/cjoc202503018 Previous Articles Next Articles

ARTICLES

电化学多组分串联合成4-硒基酰基吡唑

郭书洋^a, 何雨蒙^a, 程小敏^a, 高宇星^a, 张玉琦^a, 马豪杰^a^,^*(), 何卫民^b^,^c

^a 延安大学化学与化工学院陕西省化学反应工程重点实验室延安 716000
^b 南华大学化学化工学院衡阳 421001
^c 南京林业大学化学工程学院南京210037

收稿日期:2025-03-19 修回日期:2025-05-23 发布日期:2025-06-11
基金资助:
陕西省科学技术协会青年人才托举计划(20220609); 陕西省自然科学基础研究计划(2025JC-YBQN-129); 延安市科技计划(2022SLSFGG-005); 国家级大学生创新创业训练计划项目(202510719063); 陕西省教育厅青年创新团队(23JP193); 及陕西高校青年创新团队资助项目.

Electrochemical Multicomponent Cascade Synthesis of 4-Selenylacylpyrazoles

Shuyang Guo^a, Yumeng He^a, Xiaomin Cheng^a, Yuxing Gao^a, Yuqi Zhang^a, Haojie Ma^a^,^*(), Wei-Min He^b^,^c

^a Shaanxi Key Laboratory of Chemical Reaction Engineering, College of Chemistry and Chemical Engineering, Yan'an University, Yan'an, Shaanxi 716000
^b School of Chemistry and Chemical Engineering, University of South China, Hengyang, Hunan 421001
^c College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037

Received:2025-03-19 Revised:2025-05-23 Published:2025-06-11
Contact: *E-mail: mahj@yau.edu.cn
Supported by:
Young Talent Fund of Association for Science and Technology in Shaanxi(20220609); Natural Science Foundation Research Project of Shaanxi Province(2025JC-YBQN-129); Science and Technology Planning Project of Yan City(2022SLSFGG-005); National College Students? Innovation and Entrepreneurship Training Program(202510719063); Youth Innovation Team Project of Shaanxi Provincial Education Department(23JP193); Youth Innovation Team of Shaanxi Universities.

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Abstract

Organoselenium and pyrazole compounds are important scaffolds in pharmaceutical molecules. Herein, an electrochemical multicomponent one-pot cascade reaction of hydrazide, pentane-2,4-diones and diselenides has been established to construct 4-selenylacylpyrazoles. It is worth noting that for this efficient and green protocol, neither metal catalysts nor external oxidants are required. Moreover, this process exhibits step economy, ease of scale up and high yields to deliver various 4-selenylacylpyrazoles.

Key words: electrochemistry, green chemistry, cascade reaction, 4-selenylacylpyrazole

Cite this article

Shuyang Guo, Yumeng He, Xiaomin Cheng, Yuxing Gao, Yuqi Zhang, Haojie Ma, Wei-Min He. Electrochemical Multicomponent Cascade Synthesis of 4-Selenylacylpyrazoles[J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3807-3815.

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Fig. & Tab. 8

References 12

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Entry	Solvent	Catalyst (Dosage/equiv.)	Temp./℃	Electrolyte	Electrode	Yield^b/%
1	CH₃CN	HCl (1.0)	60	Et₄NClO₄	C(＋)/Ni()	62
2	CH₃CN	Citric acid (1.0)	60	Et₄NClO₄	C(＋)/Ni()	43
3	CH₃CN	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ni()	80
4	CH₃CN	HCl (1.0)	25	Et₄NClO₄	C(＋)/Ni()	21
5^c	CH₃CN	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ni()	No
6^d	CH₃CN	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ni()	29
7^e	CH₃CN	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ni()	61
8	CH₃CN	HCl (1.0)	80	n-Bu₄NBr	C(＋)/Ni()	63
9	CH₃CN	HCl (1.0)	80	NH₄I	C(＋)/Ni()	50
10	CH₃CN	HCl (1.0)	80	No	C(＋)/Ni()	48
11	CH₃CN	HCl (1.0)	80	n-Bu₄NI	C(＋)/Ni()	Trace
12	CH₃CN	HCl (1.0)	80	LiBF₄	C(＋)/Ni()	63
13	CH₃CN	HCl (1.0)	80	NaClO₄	C(＋)/Ni()	57
14	CH₃CN	HCl (1.0)	80	n-Bu₄NF	C(＋)/Ni()	16
15	CH₃CN	HCl (1.0)	80	NaBF₄	C(＋)/Ni()	No
16	CH₃CN	HCl (1.0)	80	Et₄NClO₄	C(＋)/Pt()	58
17	CH₃CN	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ag()	44
18	CH₃CN	HCl (1.0)	80	Et₄NClO₄	C(＋)/C()	17
19	CH₃CN	HCl (1.0)	80	Et₄NClO₄	C(＋)/Zn()	32
20	DCE	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ni()	22
21	DMSO	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ni()	No
22	DMF	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ni()	No
23	CH₃NO₂	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ni()	42
24	CH₃CN	HCl (0.5)	80	Et₄NClO₄	C(＋)/Ni()	66
25	CH₃CN	HCl (1.5)	80	Et₄NClO₄	C(＋)/Ni()	59

Entry	Solvent	Catalyst (Dosage/equiv.)	Temp./℃	Electrolyte	Electrode	Yield^b/%
1	CH₃CN	HCl (1.0)	60	Et₄NClO₄	C(＋)/Ni()	62
2	CH₃CN	Citric acid (1.0)	60	Et₄NClO₄	C(＋)/Ni()	43
3	CH₃CN	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ni()	80
4	CH₃CN	HCl (1.0)	25	Et₄NClO₄	C(＋)/Ni()	21
5^c	CH₃CN	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ni()	No
6^d	CH₃CN	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ni()	29
7^e	CH₃CN	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ni()	61
8	CH₃CN	HCl (1.0)	80	n-Bu₄NBr	C(＋)/Ni()	63
9	CH₃CN	HCl (1.0)	80	NH₄I	C(＋)/Ni()	50
10	CH₃CN	HCl (1.0)	80	No	C(＋)/Ni()	48
11	CH₃CN	HCl (1.0)	80	n-Bu₄NI	C(＋)/Ni()	Trace
12	CH₃CN	HCl (1.0)	80	LiBF₄	C(＋)/Ni()	63
13	CH₃CN	HCl (1.0)	80	NaClO₄	C(＋)/Ni()	57
14	CH₃CN	HCl (1.0)	80	n-Bu₄NF	C(＋)/Ni()	16
15	CH₃CN	HCl (1.0)	80	NaBF₄	C(＋)/Ni()	No
16	CH₃CN	HCl (1.0)	80	Et₄NClO₄	C(＋)/Pt()	58
17	CH₃CN	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ag()	44
18	CH₃CN	HCl (1.0)	80	Et₄NClO₄	C(＋)/C()	17
19	CH₃CN	HCl (1.0)	80	Et₄NClO₄	C(＋)/Zn()	32
20	DCE	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ni()	22
21	DMSO	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ni()	No
22	DMF	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ni()	No
23	CH₃NO₂	HCl (1.0)	80	Et₄NClO₄	C(＋)/Ni()	42
24	CH₃CN	HCl (0.5)	80	Et₄NClO₄	C(＋)/Ni()	66
25	CH₃CN	HCl (1.5)	80	Et₄NClO₄	C(＋)/Ni()	59

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电化学多组分串联合成4-硒基酰基吡唑

Electrochemical Multicomponent Cascade Synthesis of 4-Selenylacylpyrazoles

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