Citation: Wei-Bao He, Sai-Jie Zhao, Jing-Yang Chen, Jun Jiang, Xiang Chen, Xinhua Xu, Wei-Min He. External electrolyte-free electrochemical one-pot cascade synthesis of 4-thiocyanato-1H-pyrazoles[J]. Chinese Chemical Letters, ;2023, 34(2): 107640. doi: 10.1016/j.cclet.2022.06.063 shu

External electrolyte-free electrochemical one-pot cascade synthesis of 4-thiocyanato-1H-pyrazoles

Wei-Bao He ^a ,
Sai-Jie Zhao ^a ,
Jing-Yang Chen ^b ,
Jun Jiang ^b ,
Xiang Chen ^b ,
Xinhua Xu ^{a, *,} ,
Wei-Min He ^{b, *,}

a.
College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
b.
School of Chemistry and Chemical Engineering, University of South China, Hengyang 421001, China

xhx1581@hnu.edu.cn

weiminhe@usc.edu.cn

Received Date: 26 March 2022
Revised Date: 22 June 2022
Accepted Date: 23 June 2022
Available Online: 30 June 2022

Figures(5)

A practical synthetic method for 4-thiocyanato-1H-pyrazoles through the electrochemical cascade reaction of hydrazines, 1, 3-diones and NH₄SCN under metal-, chemical oxidant- and external electrolyte-free conditions was established. Importantly, both a gram-scale synthesis of 4-thiocyanato-1H-pyrazoles and five one-pot sequential transformations starting from hydrazine were successfully accomplished.
- Green chemistry,
- Electrochemistry,
- Cascade reaction,
- Multicomponent reaction,
- Thiocyanato
1. [1]
  C. Ma, P. Fang, Z.R. Liu, et al., Sci. Bull. 66 (2021) 2412–2429.
2. [2]
  N. Chen, H.C. Xu, Green Synth. Catal. 2 (2021) 165–178.
3. [3]
  Z. Yang, Y. Yu, L. Lai, et al., Green Synth. Catal. 2 (2021) 19–26.
4. [4]
  K. Sun, F. Xiao, B. Yu, W.M. He, Chin. J. Catal. 42 (2021) 1921–1943.
5. [5]
  J. Zhang, H. Wang, Y. Chen, et al., Chin. Chem. Lett. 31 (2020) 1576–1579.
6. [6]
  Z. Li, Q. Sun, P. Qian, et al., Chin. Chem. Lett. 31 (2020) 1855–1858.
7. [7]
  B. Huang, L. Guo, W. Xia, Green Chem. 23 (2021) 2095–2103.
8. [8]
  J.Y. Chen, H.Y. Wu, Q.W. Gui, et al., Chin. J. Catal. 42 (2021) 1445–1450.
9. [9]
  K. Niu, L. Ding, P. Zhou, et al., Green Chem. 23 (2021) 3246–3249.
10. [10]
  Y. Wu, J.Y. Chen, J. Ning, et al., Green Chem. 23 (2021) 3950–3954.
11. [11]
  J.Y. Chen, C.T. Zhong, Q.W. Gui, et al., Chin. Chem. Lett. 32 (2021) 475–479.
12. [12]
  J. Jiang, Z. Wang, W.M. He, Chin. Chem. Lett. 32 (2021) 1591–1592.
13. [13]
  X. Wang, Y. Zhang, K. Sun, J. Meng, B. Zhang, Chin. J. Org. Chem. 41 (2021) 4588–4609.
14. [14]
  Y. Wu, J.Y. Chen, H.R. Liao, et al., Green Synth. Catal. 2 (2021) 233–236.
15. [15]
  H. -B. Zhao, J.L. Zhuang, H.C. Xu, ChemSusChem 14 (2021) 1692–1695.
16. [16]
  W. Li, Y. Tang, W. Ouyang, et al., Chin. J. Org. Chem. 41 (2021) 4766–4772.
17. [17]
  S. Guo, L. Liu, K. Hu, et al., Chin. Chem. Lett. 32 (2021) 1033–1036.
18. [18]
  H. Xu, X. Meng, Y. Zheng, J. Luo, S. Huang, Chin. J. Org. Chem. 41 (2021) 4696–4703.
19. [19]
  Z.L. Wu, J.Y. Chen, X.Z. Tian, et al., Chin. Chem. Lett. 33 (2022) 1501–1504.
20. [20]
  E.A. Ilardi, E. Vitaku, J.T. Njardarson, J. Med. Chem. 57 (2014) 2832–2842.
21. [21]
  V. Burmistrov, R. Saxena, D. Pitushkin, et al., J. Med. Chem. 64 (2021) 6621–6633.
22. [22]
  W.B. He, L.Q. Gao, X.J. Chen, et al., Chin. Chem. Lett. 31 (2020) 1895–1898.
23. [23]
  J. Zhang, M. She, L. Liu, et al., Org. Lett. 23 (2021) 8396–8401.
24. [24]
  Y. Sun, R. Fu, S. Lin, et al., Biorg. Med. Chem. 29 (2021) 115890.
25. [25]
  Z.Y. Meng, C.T. Feng, L. Zhang, et al., Org. Lett. 23 (2021) 4214–4218.
26. [26]
  D. Yang, Q. Yan, E. Zhu, J. Lv, W.M. He, Chin. Chem. Lett. 33 (2022) 1798–1816.
27. [27]
  J. Wen, C. Niu, K. Yan, et al., Green Chem. 22 (2020) 1129–1133.
28. [28]
  F. Meng, H. Zhang, H. He, et al., Adv. Synth. Catal. 362 (2020) 248–254.
29. [29]
  Y. Zhang, H. Gao, J. Guo, H. Zhang, X. Yao, Chem. Commun. 57 (2021) 13166–13169.
30. [30]
  F.L. Zeng, H.L. Zhu, X.L. Chen, L.B. Qu, B. Yu, Green Chem. 23 (2021) 3677–3682.
31. [31]
  Y. Li, Z. Huang, G. Mo, et al., Chin. J. Chem. 39 (2021) 942–946.
32. [32]
  V.L.M. Silva, J. Elguero, A.M.S. Silva, Eur. J. Med. Chem. 156 (2018) 394–429.
33. [33]
  M. Ramadan, A.A. Aly, L.E.A. El-Haleem, M.B. Alshammari, S. Bräse, Molecules 26 (2021) 4995.
34. [34]
  R.F. Costa, L.C. Turones, K.V.N. Cavalcante, et al., Front. Pharmacol. 12 (2021) 666725.
35. [35]
  S.F. Chen, X.C. Liu, J.K. Xu, et al., Inorg. Chem. 60 (2021) 2839–2845.
36. [36]
  A. Sapkal, S. Kamble, ChemistrySelect 5 (2020) 12971–13026.
37. [37]
  R. Yi, W. He, Chin. J. Org. Chem. 41 (2021) 1267–1268.
38. [38]
  H. Zhuang, N. Lu, N. Ji, F. Han, C. Miao, Adv. Synth. Catal. 363 (2021) 5461–5472.
39. [39]
  D. Ali, A.K. Panday, L.H. Choudhury, J. Org. Chem. 85 (2020) 13610–13620.
40. [40]
  P. Dai, C. Li, Y. Li, et al., Asian J. Org. Chem. 9 (2020) 1585–1588.
41. [41]
  X. Mao, J. Ni, B. Xu, C. Ding, Org. Chem. Front. 7 (2020) 350–354.
42. [42]
  V.A. Kokorekin, V.M. Khodonov, S.V. Neverov, N. É. Grammatikova, V.A. Petrosyan, Russ. Chem. Bull. 70 (2021) 600–604.
43. [43]
  J. Pan, C. Liu, J. Wang, et al., Tetrahedron Lett. 77 (2021) 153253.
44. [44]
  V.A. Kokorekin, V.L. Sigacheva, V.A. Petrosyan, Tetrahedron Lett. 55 (2014) 4306–4309.
45. [45]
  T. Cui, X. Zhang, J. Lin, et al., Synlett 32 (2021) 267–272.
46. [46]
  Y. Kong, Y. Li, M. Huang, J.K. Kim, Y. Wu, Green Chem. 21 (2019) 4495–4498.
47. [47]
  L. Zeng, J. Li, J. Gao, et al., Green Chem. 22 (2020) 3416–3420.
48. [48]
  Q.W. Gui, F. Teng, S.N. Ying, et al., Chin. Chem. Lett. 31 (2020) 3241–3244.
49. [49]
  Q. Huang, L. Zhu, D. Yi, X. Zhao, W. Wei, Chin. Chem. Lett. 31 (2020) 373–376.
50. [50]
  M. Cao, Y.L. Fang, Y.C. Wang, et al., ACS Comb. Sci. 22 (2020) 268–273.
51. [51]
  B.G. Cai, Q. Li, Q. Zhang, L. Li, J. Xuan, Org. Chem. Front. 8 (2021) 5982–5987.
52. [52]
  Q.W. Gui, F. Teng, Z.C. Li, et al., Chin. Chem. Lett. 32 (2021) 1907–1910.
53. [53]
  H. Wu, X. Yu, Z. Cao, Chin. J. Org. Chem. 41 (2021) 4712–4717.
54. [54]
  N. Meng, Y. Lv, Q. Liu, et al., Chin. Chem. Lett. 32 (2021) 258–262.
55. [55]
  Z. Wang, Q. Liu, R. Liu, et al., Chin. Chem. Lett. 33 (2022) 1479–1482.
56. [56]
  M. Dyga, D. Hayrapetyan, R.K. Rit, L.J. Gooßen, Adv. Synth. Catal. 361 (2019) 3548–3553.
57. [57]
  S. Redon, A.R. Obah Kosso, J. Broggi, P. Vanelle, Tetrahedron Lett. 58 (2017) 2771–2773.
58. [58]
  L. Yang, Z.Y. Tian, C.P. Zhang, ChemistrySelect 4 (2019) 311–315.
59. [59]
  A.V. Burasov, V.A. Petrosyan, Russ. Chem. Bull. 57 (2008) 1321–1322.
60. [60]
  A. Gitkis, J.Y. Becker, Electrochim. Acta 55 (2010) 5854–5859.
1. [1]
  Liyang Qin , Luna Wu , Jinlin Long . Advancements in photocatalytic hydrogen peroxide synthesis: overcoming challenges for a sustainable future. Chinese Journal of Structural Chemistry, 2025, 44(4): 100545-100545. doi: 10.1016/j.cjsc.2025.100545
2. [2]
  Jia-Cheng Hou , Hong-Tao Ji , Yu-Han Lu , Jia-Sheng Wang , Yao-Dan Xu , Yan-Yan Zeng , Wei-Min He . Sustainable and practical semi-heterogeneous photosynthesis of 5-amino-1,2,4-thiadiazoles over WS₂/TEMPO. Chinese Chemical Letters, 2024, 35(8): 109514-. doi: 10.1016/j.cclet.2024.109514
3. [3]
  Xue Xin , Qiming Qu , Islam E. Khalil , Yuting Huang , Mo Wei , Jie Chen , Weina Zhang , Fengwei Huo , Wenjing Liu . Hetero-phase zirconia encapsulated with Au nanoparticles for boosting electrocatalytic nitrogen reduction. Chinese Chemical Letters, 2024, 35(5): 108654-. doi: 10.1016/j.cclet.2023.108654
4. [4]
  Zixuan Guo , Xiaoshuai Han , Chunmei Zhang , Shuijian He , Kunming Liu , Jiapeng Hu , Weisen Yang , Shaoju Jian , Shaohua Jiang , Gaigai Duan . Activation of biomass-derived porous carbon for supercapacitors: A review. Chinese Chemical Letters, 2024, 35(7): 109007-. doi: 10.1016/j.cclet.2023.109007
5. [5]
  Qiang Cao , Xue-Feng Cheng , Jia Wang , Chang Zhou , Liu-Jun Yang , Guan Wang , Dong-Yun Chen , Jing-Hui He , Jian-Mei Lu . Graphene from microwave-initiated upcycling of waste polyethylene for electrocatalytic reduction of chloramphenicol. Chinese Chemical Letters, 2024, 35(4): 108759-. doi: 10.1016/j.cclet.2023.108759
6. [6]
  Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
7. [7]
  Li Li , Zhi-Xin Yan , Chuan-Kun Ran , Yi Liu , Shuo Zhang , Tian-Yu Gao , Long-Fei Dai , Li-Li Liao , Jian-Heng Ye , Da-Gang Yu . Electro-reductive carboxylation of CCl bonds in unactivated alkyl chlorides and polyvinyl chloride with CO₂. Chinese Chemical Letters, 2024, 35(12): 110104-. doi: 10.1016/j.cclet.2024.110104
8. [8]
  Yan-Jiang Li , Shu-Lei Chou , Yao Xiao . Detecting dynamic structural evolution based on in-situ high-energy X-ray diffraction technology for sodium layered oxide cathodes. Chinese Chemical Letters, 2025, 36(2): 110389-. doi: 10.1016/j.cclet.2024.110389
9. [9]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
10. [10]
  Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
11. [11]
  Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
12. [12]
  Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Yongfeng Wang . Recent progress on surface chemistry Ⅰ: Assembly and reaction. Chinese Chemical Letters, 2024, 35(12): 110055-. doi: 10.1016/j.cclet.2024.110055
13. [13]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
14. [14]
  Yue Sun , Yingnan Zhu , Jiahang Si , Ruikang Zhang , Yalan Ji , Jinjie Fan , Yuze Dong . Glucose-activated nanozyme hydrogels for microenvironment modulation via cascade reaction in diabetic wound. Chinese Chemical Letters, 2025, 36(4): 110012-. doi: 10.1016/j.cclet.2024.110012
15. [15]
  Yunchao Li , Shanying Chen , Ke Qi , Kangning Huo , Shuxin Li , Jingyi Li , Ying Wei , Louzhen Fan . A New Colloid Electrophoresis Experiment Incorporating Characteristics of Inquiry Learning and Ideological and Political Education. University Chemistry, 2024, 39(2): 47-51. doi: 10.3866/PKU.DXHX202308063
16. [16]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
17. [17]
  Yongming Zhu , Huili Hu , Yuanchun Yu , Xudong Li , Peng Gao . Construction and Practice on New Form Stereoscopic Textbook of Electrochemistry for Energy Storage Science and Engineering: Taking Basic Course of Electrochemistry as an Example. University Chemistry, 2024, 39(8): 44-47. doi: 10.3866/PKU.DXHX202312086
18. [18]
  Yifei Cheng , Jiahui Yang , Wei Shao , Wanqun Zhang , Wanqun Hu , Weiwei Li , Kaiping Yang . Learning Goes Beyond the Written Word: Practical Insights from the “Leaf Electroplating” Popular Science Experiment. University Chemistry, 2024, 39(9): 319-327. doi: 10.3866/PKU.DXHX202310033
19. [19]
  Kuaibing Wang , Honglin Zhang , Wenjie Lu , Weihua Zhang . Experimental Design and Practice for Recycling and Nickel Content Detection from Waste Nickel-Metal Hydride Batteries. University Chemistry, 2024, 39(11): 335-341. doi: 10.12461/PKU.DXHX202403084
20. [20]
  Cen Zhou , Biqiong Hong , Yiting Chen . Application of Electrochemical Techniques in Supramolecular Chemistry. University Chemistry, 2025, 40(3): 308-317. doi: 10.12461/PKU.DXHX202406086

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1008)
HTML views(50)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142