Citation: Liqiang Hao, Hongyan Liu, Zheng Zhang, Fuqiang Wen, Chengcai Xia, Zengfen Pang. Cascade reaction to 1H-pyrazoles from hydrazones via sodium Ni-trite promoted dual C–C/C–N formation, annulation and aromatization with 1, 2-dichloroethane[J]. Chinese Chemical Letters, ;2021, 32(7): 2309-2312. doi: 10.1016/j.cclet.2021.02.025 shu

Cascade reaction to 1H-pyrazoles from hydrazones via sodium Ni-trite promoted dual C–C/C–N formation, annulation and aromatization with 1, 2-dichloroethane

Liqiang Hao ^a ,
Hongyan Liu ^a ,
Zheng Zhang ^a ,
Fuqiang Wen ^a ,
Chengcai Xia ^{a, *,} ,
Zengfen Pang ^{b, *,}

a.
Institute of Pharmacology, Pharmacy College, Shandong First Medical University & Shandong Academy of Medical Sciences, Tai'an 271016, China
b.
Shandong Cancer Hospital and Institute, Shandong First Medical University & Shandong Academy of Medical Sciences, Ji'nan 250117, China

xiachc@163.com

pangzf0806@163.com

Received Date: 8 December 2020
Revised Date: 2 February 2021
Accepted Date: 9 February 2021
Available Online: 15 February 2021

Figures(5)

A novel route for tandem C–C/C–N formation, annulation and aromatization of hydrazones with 1, 2-dichloroethane to synthesize 1H-pyrazoles has been developed. Furthermore, the 1, 2-dichloroethane serves as alkylation reagent in good to excellent yields. This methodology features mild reaction conditions and good functional group tolerance, providing a direct approach for the preparation of 1H-pyrazoles.
- Tandem,
- Hydrazones,
- 1, 2-Dichloroethane,
- 1H-pyrazoles,
- Annulation
1. [1]
  T.G. Le, A. Kundu, A. Ghoshal, et al., J. Med. Chem. 62 (2019) 3367-3380. doi: 10.1021/acs.jmedchem.8b01790
2. [2]
  J. Carpenter, Y. Wang, G. Wu, et al., J. Med. Chem. 60 (2017) 6166-6190. doi: 10.1021/acs.jmedchem.7b00385
3. [3]
  J.C.C. Dallagnol, E. Khajehali, E.T. van Der Westhuizen, et al., J. Med. Chem. 61 (2018) 2875-2894. doi: 10.1021/acs.jmedchem.7b01812
4. [4]
  S. Varghese, R. Rahmani, S. Russell, et al., ACS Med. Chem. Lett. 11 (2020) 278-285. doi: 10.1021/acsmedchemlett.9b00218
5. [5]
  F. Chimenti, A. Bolasco, F. Manna, et al., Chem. Biol. Drug Des. 67 (2006) 206-214. doi: 10.1111/j.1747-0285.2006.00367.x
6. [6]
  L.L. De Oliveira, R.R. Campedelli, M.C.A. Kuhn, J.F. Carpentier, O.L. Casagrande, J. Mol. Catal. A Chem. 288 (2008) 58-62. doi: 10.1016/j.molcata.2008.03.020
7. [7]
  (a) S. Peruncheralathan, T.A. Khan, H. Ila, H. Junjappa, J. Org. Chem. 70 (2005) 10030-10035;
  (b) C.M. Thompson, J.L. Poole, J.L. Cross, I. Akritopoulou-Zanze, S.W. Djuric, Molecules 16 (2011) 9161-9177;
  (c) G.W. Zhang, Y. Zhao, H.B. Ge, Angew. Chem. Int. Ed. 52 (2013) 2559-2563;
  (d) F. Punner, Y. Sohtome, M. Sodeoka, Chem. Commun. (Camb. ) 52 (2016) 14093-14096;
  (e) J. Chen, R. Properzi, D.P. Uccello, et al., Org. Lett. 16 (2014) 4146-4149;
  (f) J.D. Kirkham, S.J. Edeson, S. Stokes, J.P.A. Harrity, Org. Lett. 14 (2012) 5354-5357;
  (g) J. Schranck, X.F. Wu, H. Neumann, M. Beller, Chem. Eur. J. 18 (2012) 4827-4831.
8. [8]
  J. Comas-Barcel, R.S. Foster, B. Fiser, E. Gomez-Bengoa, J.P.A. Harrity, Chem. Eur. J. 20 (2014) 1-8. doi: 10.1002/chin.201527170
9. [9]
  N. Panda, A.K. Jena, J. Org. Chem. 77 (2012) 9401-9406. doi: 10.1021/jo301770k
10. [10]
  G.D. Wang, J. Sun, K. Wang, et al., Org. Chem. Front. 6 (2019) 1608-1612. doi: 10.1039/c9qo00367c
11. [11]
  L.Q. Hao, G.D. Wang, J. Sun, et al., Adv. Synth. Catal. 362 (2020) 1657-1662. doi: 10.1002/adsc.201901563
1. [1]
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2. [2]
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3. [3]
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4. [4]
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5. [5]
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6. [6]
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7. [7]
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9. [9]
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10. [10]
  Zan Chen , Yi Wang , Yuxuan Zhou , Yunlang Li , Rong Xiong , Wenting Huang , Huanfeng Jiang , Wanqing Wu . Selective synthesis of [6-6-7]/[6-6-6] core polycyclic heterocycles via Lewis acid-mediated cascade annulation of 1,6-enynols with aminonitriles. Chinese Chemical Letters, 2026, 37(6): 111718-. doi: 10.1016/j.cclet.2025.111718
11. [11]
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12. [12]
  Yuhao Guo , Na Li , Tingjiang Yan . Tandem catalysis for photoreduction of CO2 into multi-carbon fuels on atomically thin dual-metal phosphochalcogenides. Chinese Journal of Structural Chemistry, 2024, 43(7): 100320-100320. doi: 10.1016/j.cjsc.2024.100320
13. [13]
  Weikang Wang , Lele Wang , Qinqin Liu . CO2 valorization to amides via S-scheme photocatalysis with tandem carbonylation. Chinese Journal of Structural Chemistry, 2025, 44(12): 100718-100718. doi: 10.1016/j.cjsc.2025.100718
14. [14]
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15. [15]
  Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
16. [16]
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17. [17]
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18. [18]
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19. [19]
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20. [20]
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沈阳化工大学材料科学与工程学院沈阳 110142