Citation: Guoping Yang, Xuanjie Xie, Mengyuan Cheng, Xiaofei Gao, Xiaoling Lin, Ke Li, Yuanyuan Cheng, Yufeng Liu. H₄SiW₁₂O₄₀-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides: An efficient synthesis of 3, 4-disubstituted 1H-pyrazoles[J]. Chinese Chemical Letters, ;2022, 33(3): 1483-1487. doi: 10.1016/j.cclet.2021.08.037 shu

H₄SiW₁₂O₄₀-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides: An efficient synthesis of 3, 4-disubstituted 1H-pyrazoles

Guoping Yang ^{a, *,} ,
Xuanjie Xie ^a ,
Mengyuan Cheng ^b ,
Xiaofei Gao ^a ,
Xiaoling Lin ^a ,
Ke Li ^a ,
Yuanyuan Cheng ^{a, *,} ,
Yufeng Liu ^{a, *,}

a.
Jiangxi Key Laboratory for Mass Spectrometry and Instrumentation, Jiangxi Province Key Laboratory of Synthetic Chemistry, East China University of Technology, Nanchang 330013, China
b.
Henan Key Laboratory of Polyoxometalate Chemistry, College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, China

erick@ecut.edu.cn

201860095@ecut.edu.cn

yfliu@ecut.edu.cn

Received Date: 24 June 2021
Revised Date: 6 August 2021
Accepted Date: 8 August 2021
Available Online: 12 August 2021

Figures(6)

A simple and efficient method for the synthesis of pyrazoles through a silicotungstic acid (H₄SiW₁₂O₄₀)-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides has been developed. Various epoxides/aldehydes were smoothly reacted with sulfonyl hydrazides to furnish regioselectivity 3, 4-disubstituted 1H-pyrazoles. The application of such an earth-abundant, readily accessible, and nontoxic catalyst provides a green approach for the construction of 3, 4-disubstituted 1H-pyrazoles. A plausible reaction mechanism has been proposed on the basis of control experiments, GC-MS and DFT calculations.
- Silicotungstic acid,
- Epoxides,
- Aldehydes,
- Sulfonyl hydrazides,
- 3, 4-Disubstituted 1H-pyrazoles
1. [1]
  A. Ansari, A. Ali, M. Asif, et al., New J. Chem. 41(2017) 16-41. doi: 10.1039/C6NJ03181A
2. [2]
  J.V. Faria, P.F. Vegi, A.G.C. Miguita, et al., Biorg. Med. Chem. 25(2017) 5891-5903. doi: 10.1016/j.bmc.2017.09.035
3. [3]
  D. Havrylyuk, B. Zimenkovsky, O. Vasylenko, et al., J. Med. Chem. 55(2012) 8630-8641. doi: 10.1021/jm300789g
4. [4]
  Ş. G. Küçükgüzel, S. Şenkardeş, Eur. J. Med. Chem. 97(2015) 786-815. doi: 10.1016/j.ejmech.2014.11.059
5. [5]
  V. Kumar, K. Kaur, G.K. Gupta, et al., Eur. J. Med. Chem. 69(2013) 735-753. doi: 10.1016/j.ejmech.2013.08.053
6. [6]
  X.H. Lv, Z.L. Ren, D.D. Li, et al., Chin. Chem. Lett. 28(2017) 377-382. doi: 10.1016/j.cclet.2016.10.029
7. [7]
  L. Catala, K. Wurst, D.B. Amabilino, et al., J. Mater. Chem. 16(2006) 2736-2745. doi: 10.1039/b604598g
8. [8]
  I.L. Dalinger, A.V. Kormanov, K.Y. Suponitsky, et al., Chem. Asian J. 13(2018) 1165-1172. doi: 10.1002/asia.201800214
9. [9]
  A.L. Rheingold, L.N. Zakharov, S. Trofimenko, Inorg. Chem. 42(2003) 827-833. doi: 10.1021/ic0205280
10. [10]
  U.P. Singh, S. Kashyap, H.J. Singh, et al., CrystEngComm 13(2011) 4110-4120. doi: 10.1039/c0ce00820f
11. [11]
  P. Yin, C. He, J.N.M. Shreeve, J. Mater. Chem. A 4(2016) 1514-1519. doi: 10.1039/C5TA09999D
12. [12]
  S. Fustero, M. Sánchez-Roselló, P. Barrio, et al., Chem. Rev. 111(2011) 6984-7034. doi: 10.1021/cr2000459
13. [13]
  Y.L. Janin, Chem. Rev. 112(2012) 3924-3958. doi: 10.1021/cr200427q
14. [14]
  M. Li, B.X. Zhao, Eur. J. Med. Chem. 85(2014) 311-340. doi: 10.1016/j.ejmech.2014.07.102
15. [15]
  P. Zhao, Z. Zeng, X. Feng, et al., Chin. Chem. Lett. 32(2021) 132-135. doi: 10.1016/j.cclet.2020.11.053
16. [16]
  L. Hao, H. Liu, Z. Zhang, et al., Chin. Chem. Lett. 32(2021) 2309-2312. doi: 10.1016/j.cclet.2021.02.025
17. [17]
  M. Zora, A. Kivrak, C. Yazici, J. Org. Chem. 76(2011) 6726-6742. doi: 10.1021/jo201119e
18. [18]
  B.H. Zhang, L.S. Lei, S.Z. Liu, et al., Chem. Commun. 53(2017) 8545-8548. doi: 10.1039/C7CC04610C
19. [19]
  Q. Wang, L. He, K.K. Li, et al., Org. Lett. 19(2017) 658-661. doi: 10.1021/acs.orglett.6b03822
20. [20]
  G. Ji, X. Wang, S. Zhang, et al., Chem. Commun. 50(2014) 4361-4363. doi: 10.1039/C4CC01280A
21. [21]
  X. Deng, N.S. Mani, Org. Lett. 10(2008) 1307-1310. doi: 10.1021/ol800200j
22. [22]
  J. Sun, J.K. Qiu, Y.L. Zhu, et al., J. Org. Chem. 80(2015) 8217-8224. doi: 10.1021/acs.joc.5b01280
23. [23]
  S. Zhao, K. Chen, L. Zhang, et al., Adv. Synth. Catal. 362(2020) 3516-3541. doi: 10.1002/adsc.202000466
24. [24]
  C. Zhu, H. Zeng, C. Liu, et al., Org. Lett. 22(2020) 809-813. doi: 10.1021/acs.orglett.9b04228
25. [25]
  Y.Q. Jiang, J. Li, Z.W. Feng, et al., Adv. Synth. Catal. 362(2020) 2609-2614. doi: 10.1002/adsc.202000233
26. [26]
  Z. Wang, W.M. He, Chin. J. Org. Chem. 39(2019) 3594-3595. doi: 10.6023/cjoc201900002
27. [27]
  J. Zhang, Y. Shao, H. Wang, et al., Org. Lett. 16(2014) 3312-3315. doi: 10.1021/ol501312s
28. [28]
  G.P. Yang, S.X. Shang, B. Yu, et al., Inorg. Chem. Front. 5(2018) 2472-2477. doi: 10.1039/C8QI00678D
29. [29]
  G.P. Yang, X. He, B. Yu, et al., Appl. Organomet. Chem. 32(2018) e4532. doi: 10.1002/aoc.4532
30. [30]
  T. Zhang, Y. Meng, J. Lu, et al., Adv. Synth. Catal. 360(2018) 3063-3068. doi: 10.1002/adsc.201701200
31. [31]
  H. Zhang, Q. Wei, G. Zhu, et al., Tetrahedron Lett. 57(2016) 2633-2637. doi: 10.1016/j.tetlet.2016.05.020
32. [32]
  J. Wen, Y. Fu, R.Y. Zhang, et al., Tetrahedron 67(2011) 9618-9621. doi: 10.1016/j.tet.2011.09.074
33. [33]
  L. Tang, M. Ma, Q. Zhang, et al., Adv. Synth. Catal. 359(2017) 2610-2620. doi: 10.1002/adsc.201700196
34. [34]
  Y. Guo, G. Wang, L. Wei, et al., J. Org. Chem. 84(2019) 2984-2990. doi: 10.1021/acs.joc.8b02897
35. [35]
  M. Yoshimatsu, K. Ohta, N. Takahashi, Chem. Eur J. 18(2012) 15602-15606. doi: 10.1002/chem.201202828
36. [36]
  S.X. Xu, L. Hao, T. Wang, et al., Org. Biomol. Chem. 11(2013) 294-298. doi: 10.1039/C2OB27016A
37. [37]
  L. Wu, M. Shi, J. Org. Chem. 75(2010) 2296-2301. doi: 10.1021/jo100105k
38. [38]
  W.M. Shu, K.L. Zheng, J.R. Ma, et al., Org. Lett. 17(2015) 1914-1917. doi: 10.1021/acs.orglett.5b00605
39. [39]
  M.C. Pérez-Aguilar, C. Valdés, Angew. Chem. Int. Ed. 52(2013) 7219-7223. doi: 10.1002/anie.201301284
40. [40]
  G.P. Yang, Y.F. Liu, K. Li, et al., Chin. Chem. Lett. 31(2020) 3233-3236. doi: 10.1016/j.cclet.2020.07.018
41. [41]
  G.P. Yang, Y.F. Liu, X.L. Lin, et al., Chin. Chem. Lett. 33(2022) 354-357. doi: 10.1016/j.cclet.2021.05.008
42. [42]
  G.P. Yang, X. Wu, B. Yu, et al., ACS Sustain. Chem. Eng. 7(2019) 3727-3732. doi: 10.1021/acssuschemeng.8b06445
43. [43]
  M.T. Lv, Y.F. Liu, K. Li, et al., Tetrahedron Lett. 65(2021) 152757. doi: 10.1016/j.tetlet.2020.152757
44. [44]
  M. Smith, R. Hunter, N. Stellenboom, et al., Biochim. Biophys. Acta Gen. Subj. 1860(2016) 1439-1449. doi: 10.1016/j.bbagen.2016.03.032
45. [45]
  Z. Lian, B.N. Bhawal, P. Yu, et al., Science 356(2017) 1059-1063. doi: 10.1126/science.aam9041
46. [46]
  Y. Shi, S. Li, Y. Lu, et al., Chem. Commun. 56(2020) 2131-2134. doi: 10.1039/C9CC09262E
47. [47]
  J. Meinwald, S.S. Labana, M.S. Chadha, J. Am. Chem. Soc. 85(1963) 582-585. doi: 10.1021/ja00888a022
1. [1]
  Tian-Yu Gao , Xiao-Yan Mo , Shu-Rong Zhang , Yuan-Xu Jiang , Shu-Ping Luo , Jian-Heng Ye , Da-Gang Yu . Visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO₂. Chinese Chemical Letters, 2024, 35(7): 109364-. doi: 10.1016/j.cclet.2023.109364
2. [2]
  Hong-Tao Ji , Yu-Han Lu , Yan-Ting Liu , Yu-Lin Huang , Jiang-Feng Tian , Feng Liu , Yan-Yan Zeng , Hai-Yan Yang , Yong-Hong Zhang , Wei-Min He . Nd@C₃N₄-photoredox/chlorine dual catalyzed synthesis and evaluation of antitumor activities of 4-alkylated sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110568-. doi: 10.1016/j.cclet.2024.110568
3. [3]
  Lei Shen , Yang Zhang , Linlin Zhang , Chuanwang Liu , Zhixian Ma , Kangjiang Liang , Chengfeng Xia . Phenylhydrazone anions excitation for the photochemical carbonylation of aryl iodides with aldehydes. Chinese Chemical Letters, 2024, 35(4): 108742-. doi: 10.1016/j.cclet.2023.108742
4. [4]
  Kun Tang , Fen Su , Shijie Pan , Fengfei Lu , Zhongfu Luo , Fengrui Che , Xingxing Wu , Yonggui Robin Chi . Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings. Chinese Chemical Letters, 2024, 35(9): 109495-. doi: 10.1016/j.cclet.2024.109495
5. [5]
  Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250
6. [6]
  Zhikang Wu , Guoyong Dai , Qi Li , Zheyu Wei , Shi Ru , Jianda Li , Hongli Jia , Dejin Zang , Mirjana Čolović , Yongge Wei . POV-based molecular catalysts for highly efficient esterification of alcohols with aldehydes as acylating agents. Chinese Chemical Letters, 2024, 35(8): 109061-. doi: 10.1016/j.cclet.2023.109061
7. [7]
  Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520
8. [8]
  Jinyuan Cui , Tingting Yang , Teng Xu , Jin Lin , Kunlong Liu , Pengxin Liu . Hydrogen spillover enhances the selective hydrogenation of α,β-unsaturated aldehydes on the Cu-O-Ce interface. Chinese Journal of Structural Chemistry, 2025, 44(1): 100438-100438. doi: 10.1016/j.cjsc.2024.100438
9. [9]
  Xun Zhu , Chenchen Zhang , Yingying Li , Yin Lu , Na Huang , Dawei Wang . Degradation of perfluorooctanoic acid by inductively heated Fenton-like process over the Fe₃O₄/MIL-101 composite. Chinese Chemical Letters, 2024, 35(12): 109753-. doi: 10.1016/j.cclet.2024.109753
10. [10]
  Cailing Wu , Shaojie Wu , Qifei Huang , Kai Sun , Xianqiang Huang , Jianji Wang , Bing Yu . Potassium-modified carbon nitride photocatalyzed-aminoacylation of N-sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110250-. doi: 10.1016/j.cclet.2024.110250
11. [11]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
12. [12]
  Jing LIANG , Qian WANG , Junfeng BAI . Synthesis and structures of cdq-topological quaternary and (4, 4, 8)-c topological quinary Zn-MOFs with both oxalic acid and triazole ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2186-2192. doi: 10.11862/CJIC.20240177
13. [13]
  Weizhong LING , Xiangyun CHEN , Wenjing LIU , Yingkai HUANG , Yu LI . Syntheses, crystal structures, and catalytic properties of three zinc(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) coordination polymers constructed from 5-(4-carboxyphenoxy)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1803-1810. doi: 10.11862/CJIC.20240068
14. [14]
  Junying LI , Xinyan CHEN , Xihui DIAO , Muhammad Yaseen , Chao CHEN , Hao WANG , Chuansong QI , Wei LI . Chiral fluorescent sensor Tb³⁺@Cd-CP based on camphoric acid for the enantioselective recognition of R- and S-propylene glycol. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2497-2504. doi: 10.11862/CJIC.20240084
15. [15]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
16. [16]
  Haitao Yin , Liang Meng , Li Li , Jiamu Xiao , Longrui Liang , Nannan Huang , Yansong Shi , Angang Zhao , Jingwen Hou . Polydopamine-modified biochar supported polylactic acid and zero-valent iron affects the functional microbial community structure for 1,1,1-trichloroethane removal in simulated groundwater. Chinese Chemical Letters, 2025, 36(1): 110313-. doi: 10.1016/j.cclet.2024.110313
17. [17]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
18. [18]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
19. [19]
  Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
20. [20]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792

Get Citation

PDF

XML

Metrics

PDF Downloads(11)
Abstract views(653)
HTML views(143)

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

H4SiW12O40-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides: An efficient synthesis of 3, 4-disubstituted 1H-pyrazoles

Metrics

通讯作者: 陈斌, bchen63@163.com

H₄SiW₁₂O₄₀-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides: An efficient synthesis of 3, 4-disubstituted 1H-pyrazoles