Citation: Chen Ying, Zhu Jianan, Zhao Shengyin. Chloroamine-T Promoted Three-Component Reaction of Aldehydes, Hydrazines and Fumarate Esters for the Construction of Tetra-substituted Pyrazole Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(7): 1923-1929. doi: 10.6023/cjoc201901014 shu

Chloroamine-T Promoted Three-Component Reaction of Aldehydes, Hydrazines and Fumarate Esters for the Construction of Tetra-substituted Pyrazole Derivatives

Key Laboratory of Science and Technology of Exo-Textile, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620

Corresponding author: Zhao Shengyin, syzhao8@dhu.edu.cn
Received Date: 10 January 2019
Revised Date: 18 March 2019
Available Online: 9 July 2019
Fund Project: Project supported by the Natural Science Foundation of Shanghai City (No. 15ZR1401400)the Natural Science Foundation of Shanghai City 15ZR1401400

Figures(4)

Pyrazoles, a class of five-membered nitrogen-containing heterocyclic compounds, showed antibacterial, anticancer and antioxidative activity, and so on. They also served as important intermediates in organic synthesis. To develop the general and straightforward methods to their synthesis is of great significance. In this paper, a series of tetra-substituted pyrazoles were synthesized from aldehydes, hydrazines and fumarate esters by three-component[3+2] cycloaddition reaction in the presence of chloroamine-T with 60%~87% yields. Their structures were confirmed by ¹H NMR, ¹³C NMR, IR and HRMS analysis.
- aldehyde,
- aldehyde,
- fumarate ester,
- chloroamine-T,
- pyrazole
1. [1]
  For biological reviews: (a) Silva, V. L. M.; Elguero, J.; Silva, J.M. S. Eur. J. Med. Chem. 2018, 156, 394.
  (b) Karrouchi, K.; Radi, S.; Ramli, Y.; Taoufik, J.; Mabkhot, Y. N.; Al-aizari, F. A.; Ansar, M. Molecules 2018, 23, 134/1.
  (c) Faria, J. V.; Vegi, P. F.; Miguita, A. G. C.; dos Santos, M. S.; Boechat, N.; Bernardino, A.M. R. Bioorg. Med. Chem. 2017, 25, 5891.
  (d) Ansari, A.; Ali, A.; Asif, M.; Shamsuzzaman New J. Chem. 2017, 41, 16.
  (e) Gangulv, S.; Jacob, S. K. Mini-Rev. Med. Chem. 2017, 17, 959.
2. [2]
  For synthetic reviews: (a) Liu, S. Y.; Bao, X. Z.; Wang, B. M. Chem. Commun. 2018, 54, 11515.
  (b) Maddila, S.; Jonnalagadda, S. B.; Gangu, K. K.; Maddila, S. N. Curr. Org. Synth. 2017, 14, 634.
  (c) Khidre, R. E.; Abdel-Wahab, B. F.; Farahat, A. A.; Mohamed, H. A. J. Heterocycl. Chem. 2016, 53, 13.
  (d) Li, M.; Zhao, B. X. Eur. J. Med. Chem. 2014, 85, 311.
3. [3]
  (a) Kumar, V.; Kaur, K.; Gupta, G. K.; Sharma, A. K. Eur. J. Med. Chem. 2013, 69, 735.
  (b) Schmidt, A.; Dreger, A. Curr. Org. Chem. 2011, 15, 1423.
4. [4]
  (a) Domling, A.; Wang, W.; Wang, K. Chem. Rev. 2012, 112, 3083.
  (b) Wan, J.-P.; Liu, Y.-Y. RSC Adv. 2012, 2, 9763.
  (c) Liu, Y.-Y.; Wang, H.; Wan, J.-P. Asian J. Org. Chem. 2013, 2, 374.
  (d) Wan, J.-P.; Gan, L.; Liu, Y.-Y. Org. Biomol. Chem. 2017, 15, 9031.
  (e) Rotstein, B.H..; Zaretsky, S.; Rai, V.; Yudin, A. K. Chem. Rev. 2014, 114, 8323.
5. [5]
6. [6]
  Yavari, I.; Khalili, G.; Mirzaei, A. Helv. Chim. Acta 2010, 93, 277. doi: 10.1002/hlca.200900246
7. [7]
  Ma, C.; Li, Y.; Wen, P.; Yan, R.; Ren, Z.; Huang, G. Synlett 2011, 1321.
8. [8]
  Safaei, S.; Mohammadpoor-Baltork, I.; Khosropour, A. R.; Moghadam, M.; Tangestaninejad, S.; Mirkhani, V. Adv. Synth. Catal. 2012, 354, 3095. doi: 10.1002/adsc.201200191
9. [9]
  Rai, L.K.M.; Hassner, A. Synth. Commun. 1989, 19, 2799 doi: 10.1080/00397918908052667
10. [10]
  Jedlovska, E.; Fisera, L.; Liptaj, T. Chem. Pap. 2005, 59, 354.
11. [11]
  Kumar, G. V.; Khatoon, B. B. A.; Kumar, K. A. J. Chem. Pharm. Res. 2015, 7, 854.
12. [12]
  Zhu, J. N.; Yang, Z. H.; Qi, M.; Zhao, S. Y. Adv. Synth. Catal. 2019, 361, 868. doi: 10.1002/adsc.201801260
13. [13]
  Liu, G. N.; Luo, R. H.; Zhou, Y.; Zhang, X. J.; Li, J.; Yang, L. M.; Zheng, Y. T.; Liu, H. Molecules 2016, 21, 1198. doi: 10.3390/molecules21091198
14. [14]
  Pratapan, S.; Scaria, P. M.; Bhattacharyya, K.; Das, P. K.; George, M. V. J. Org. Chem. 1986, 51, 1972 doi: 10.1021/jo00361a006
15. [15]
  Safaei, S.; Mohammadpoor-Baltork, I.; Khosropour, A. R.; Moghadam, M.; Tangestaninejad, S.; Mirkhani, V. New J. Chem. 2013, 37, 2037. doi: 10.1039/c3nj40756j
16. [16]
  Mertzanos, G. E.; Alexandrou, N. E.; Tsoleridis, C. A.; Mitkidou, S.; Stephanidou-Stephanatou, J. Heterocycles 1994, 37, 967. doi: 10.3987/COM-93-S97
17. [17]
  Tewari, R. S.; Parihar, P. Tetrahedron 1983, 39, 129. doi: 10.1016/S0040-4020(01)97638-0
18. [18]
  Jones, R. G.; Whitehead, C. W. J. Org. Chem. 1955, 20, 1342. doi: 10.1021/jo01127a008
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