Citation: Liu Qishun, Lü Yufen, Bao Pengli, Yue Huilan, Wei Wei. Recent Progress in the Synthesis of N-Substituted-1, 2, 3-triazoles[J]. Chinese Journal of Organic Chemistry, ;2020, 40(12): 4015-4030. doi: 10.6023/cjoc202008042 shu

Recent Progress in the Synthesis of N-Substituted-1, 2, 3-triazoles

Liu Qishun ^a ,
Lü Yufen ^a ,
Bao Pengli ^a,, ,
Yue Huilan ^b,, ,
Wei Wei ^a,b,,

a.
School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165
b.
Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining 810008

Corresponding author: Bao Pengli, baopengli1992@163.com Yue Huilan, hlyue@nwipb.cas.cn Wei Wei, weiweiqfnu@163.com
Received Date: 24 August 2020
Revised Date: 28 September 2020
Available Online: 13 October 2020
Fund Project: Project supported by the Youth Innovation and Technology Project of Shandong Province (No. 2019KJC021), the Natural Science Foundation of Shandong Province (No. ZR2018MB009) and the International Cooperation Project of Qinghai Province (No. 2018-HZ-806)the International Cooperation Project of Qinghai Province 2018-HZ-806the Youth Innovation and Technology Project of Shandong Province 2019KJC021the Natural Science Foundation of Shandong Province ZR2018MB009

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N-Substituted-1, 2, 3-triazoles are an important class of nitrogen-containing hetrocyclic compounds, which exhibited wide applications in various fields such as medicinal chemistry, synthetic chemistry and materials. Therefore, their synthetic methods have attracted great attention of chemists. Herein, the recent research progress in the synthesis of N-substituted-1, 2, 3-triazoles is summarized. The synthetic routes and reaction mechanisms from raw materials such as azide compounds, diazo compounds, TsNHNH₂, hydrazones and NH-1, 2, 3-triazoles are introduced and reviewed, respectively. Finally, the future development of this field is also prospected.
- N-substituted-1, 2, 3-triazole,
- azide compound,
- hydrazone,
- TsNHNH₂,
- diazo compound,
- NH-1, 2, 3-triazole
1. [1]
2. [2]
  (a) Chu, C.; Liu, R. Chem. Soc. Rev. 2011, 40, 2177.
  (b) Lau, Y. H.; Rutledge, P. J.; Watkinson, M.; Todd, M. H. Chem. Soc. Rev. 2011, 40, 2848.
  (c) Johnson, T. C.; Totty, W. G.; Wills, M. Org. Lett. 2012, 14, 5230.
3. [3]
  (a) Astruc, D.; Liang, L.; Rapakousiou, A.; Ruiz, J. Chem. Res. 2012, 45, 630.
  (b) Muller, T.; Bräse, S. Angew. Chem., Int. Ed. 2011, 50, 11844.
4. [4]
  (a) Wang, W.; Peng, X.; Wei, F.; Tung, C.-H.; Xu, Z. Angew. Chem., Int. Ed. 2016, 55, 649.
  (b) Cheung, K. P. S.; Tsui, G. C. Org. Lett. 2017, 19, 2881.
5. [5]
  (a) Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Chem. Rev. 2013, 113, 4905.
  (b) Wang, K.; Chen, M.; Wang, Q.; Shi, X.; Lee, J. K. J. Org. Chem. 2013, 78, 7249.
6. [6]
7. [7]
  (a) Quan, X. J.; Ren, Z. H.; Wang, Y. Y.; Guan, Z. H. Org. Lett. 2014, 16, 5728.
  (b) Chen, C. Y.; Lee, P. H.; Lin, Y. Y.; Yu, W. T.; Hu, W. P.; Hsu, C. C.; Lin, Y. T.; Chang, L. S.; Hsiao, C. T.; Wang, J. J.; Chung, M. L. Bioorg. Med. Chem. Lett. 2013, 23, 6854.
8. [8]
9. [9]
  Kalisiak, J.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2008, 10, 3171. doi: 10.1021/ol8006748
10. [10]
  Zhang, Y.; Li, X.; Li, J.; Chen, J.; Meng, X.; Zhao, M.; Chen, B. Org. Lett. 2012, 14, 26. doi: 10.1021/ol202718d
11. [11]
  Kamijo, S.; Jin, T.; Huo, Z. B.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 7786. doi: 10.1021/ja034191s
12. [12]
  Phanindrudu, M.; Tiwari, D. K.; Aravilli, V. K.; Bhardwaj, K. C.; Sabapathi, G.; Likhar, P. R. Eur. J. Org. Chem. 2016, 27, 4629.
13. [13]
  Shen, T.; Huang, X.; Liang, Y.-F.; Jiao, N. Org. Lett. 2015, 17, 6186. doi: 10.1021/acs.orglett.5b03179
14. [14]
  Chen, J.; Liang, T.; Zhao, H.; Lin, C.; Chen, L.; Zhang, M. Org. Biomol. Chem. 2019, 17, 4843. doi: 10.1039/C9OB00686A
15. [15]
  Bao, P. L.; Yue, H.; Meng, N.; Zhao, X.; Li, J.; Wei, W. Org. Lett. 2019, 21, 7218. doi: 10.1021/acs.orglett.9b02295
16. [16]
  Bao, P. L.; Meng, N.; Lv, Y.; Yue, H.; Li, J.; Wei, W. Org. Chem. Front. 2019, 6, 3983. doi: 10.1039/C9QO01277J
17. [17]
  Virant, M.; Košmrlj, J. J. Org. Chem. 2019, 84, 14030. doi: 10.1021/acs.joc.9b02197
18. [18]
  Cui, F.; Chen, J.; Mo, Z.; Su, S.; Chen, Y.; Ma, X.; Tang, H.; Wang, H.; Pan, Y.; Xu, Y. Org. Lett. 2018, 20, 925. doi: 10.1021/acs.orglett.7b03734
19. [19]
  Jana, S.; Thomas, J.; Dehaen, W. J. Org. Chem. 2016, 81, 12426. doi: 10.1021/acs.joc.6b02607
20. [20]
  Chen, Y. F.; Nie, G.; Zhang, Q.; Ma, S.; Li, H.; Hu, Q. Q. Org. Lett. 2015, 17, 1118. doi: 10.1021/ol503687w
21. [21]
  Liu, Y.; Nie, G.; Zhou, Z.; Jia, L.; Chen, Y. J. Org. Chem. 2017, 82, 9198. doi: 10.1021/acs.joc.7b01429
22. [22]
  Kumar, N.; Ansari, M. Y.; Kumart, A. Chem. Commun. 2018, 54, 2627. doi: 10.1039/C7CC09934G
23. [23]
  Wei, F.; Li, H.; Song, C.; Ma, Y.; Zhou, L.; Tung, C.-H.; Xu, Z. H. Org. Lett. 2015, 17, 2860. doi: 10.1021/acs.orglett.5b01342
24. [24]
  Wang, W. G.; Peng, X. L.; Wei, F.; Tung, C. H.; Xu, Z. H. Angew. Chem., Int. Ed. 2016, 55, 649. doi: 10.1002/anie.201509124
25. [25]
  (a) Wang, W.; Wei, F.; Ma, Y.; Tung, C.-H.; Xu, Z. H. Org. Lett. 2016, 18, 4158.
  (b) Wang, W.; Lin, Y.; Ma, Y.; Tung, C.-H.; Xu, Z. H. Org. Lett. 2018, 20, 2956.
26. [26]
  Shang, J. Q.; Fu, H.; Li, Y.; Yang, T.; Gao, C. Z.; Li, Y. M. Tetrahedron 2019, 75, 253. doi: 10.1016/j.tet.2018.11.054
27. [27]
  (a) Chen, Y.; Liu, Y.; Petersena, J. L.; Shi, X. Chem. Commun. 2008, 3254.
  (b) Liu, Y.; Yan, W.; Chen, Y.; Petersen, J. L.; Shi, X. Org. Lett. 2008, 10, 5389.
  (c) Wang, X.; Sidhu, K.; Zhang, L.; Campbell, S.; Haddad, N.; Reeves, D. C.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2009, 11, 5490.
  (d) Zhang, C.; Zheng, L.; Yan, Q.; Hu, Q.; Jia, F.; Chen, Y. ChemistrySelect 2018, 3, 10277.
28. [28]
  Aruri, H.; Singh, U.; Sharma, S.; Gudup, S.; Bhogal, M.; Kumar, S.; Singh, D.; Gupta, V. K.; Kant, R.; Vishwakarma, R. A.; Singh. P. P. J. Org. Chem. 2015, 80, 1929. doi: 10.1021/jo502477r
29. [29]
  Deng, X. C.; Lei, X.; Nie, G.; Jia, L. H.; Li, Y. X.; Chen, Y. F. J. Org. Chem. 2017, 82, 6163. doi: 10.1021/acs.joc.7b00752
30. [30]
  Zhang, L. L.; Yi, H.; Wang, J.; Lei, A. W. J. Org. Chem. 2017, 82, 10704. doi: 10.1021/acs.joc.7b01841
31. [31]
  Wu, J.; Zhou, Y.; Zhou, Y.; Chiang, C. W.; Lei, A. W. ACS Catal. 2017, 7, 8320. doi: 10.1021/acscatal.7b03551
32. [32]
  Berthold, D.; Breit, B. Org. Lett. 2018, 20, 598. doi: 10.1021/acs.orglett.7b03708
33. [33]
  Luo, G. L.; Sun, C. Y.; Li, Y.; Li, X. X.; Zhao, Z. RSC Adv. 2018, 8, 27610. doi: 10.1039/C8RA04790A
34. [34]
  Chen, Z.; Cao, G.; Song, J.; Ren, H. Chin. J. Chem. 2017, 35, 1797. doi: 10.1002/cjoc.201700459
35. [35]
  Hanselmann, R.; Job, G. E.; Johnson, G.; Lou, R.; Martynow, J. G.; Reeve, M. M. Org. Process Res. Dev. 2010, 14, 152. doi: 10.1021/op900252a
36. [36]
  van Berkel, S. S.; Brauch, S.; Gabriel, L.; Henze, M.; Stark, S.; Va-silev, D.; Wessjohann, L. A.; Abbas, M.; Westermann, B. Angew. Chem., Int. Ed. 2012, 51, 5343. doi: 10.1002/anie.201108850
37. [37]
  (a) Fçhlisch, B.; Flogaus, R. Synthesis 1984, 734.
  (b) Bangalore, J.; Llavona, L.; Concellon, J. M.; Yus, M. J. Chem. Soc., Perkin Trans. 1 1991, 297.
38. [38]
  (a) Chen, Z.; Yan, Q.; Liu, Z.; Xu, Y.; Zhang, Y. Angew. Chem., Int. Ed. 2013, 52, 13324.
  (b) Chen, Z.; Yan, Q.; Yi, H.; Liu, Z.; Lei, A.; Zhang, Y. Chem.-Eur. J. 2014, 20, 13692.
39. [39]
  Cai, Z.-J.; Lu, X.-M.; Zi, Y.; Yang, C.; Shen, L.-J.; Li, J.; Wang, S.-Y.; Ji, S.-J. Org. Lett. 2014, 16, 5108. doi: 10.1021/ol502431b
40. [40]
  Guru, M. M.; Punniyamurthy, T. J. Org. Chem. 2012, 77, 5063. doi: 10.1021/jo300592t
41. [41]
  Chen, Z.; Yan, Q.; Liu, Z.; Zhang, Y. Chem.-Eur. J. 2014, 20, 17535.
42. [42]
  (a) Wan, J.-P.; Cao, S.; Liu, Y. J. Org. Chem. 2015, 80, 9028.
  (b) Thomas, J.; Goyvaerts, V.; Liekens, S.; Dehaen, W. Chem.-Eur. J. 2016, 22, 9966.
43. [43]
  Li, Y.-J.; Li, X.; Zhang, S.-X.; Zhao, Y.-L.; Liu, Q. Chem. Commun. 2015, 51, 11564. doi: 10.1039/C5CC02092A
44. [44]
  Wang, S.; Yang, L.-J.; Zeng, J.-L.; Zheng, Y.; Ma, J.-A. Org. Chem. Front. 2015, 2, 1468. doi: 10.1039/C5QO00219B
45. [45]
  Kiselyov, A. S. Tetrahedron Lett. 2006, 47, 2631. doi: 10.1016/j.tetlet.2006.02.030
46. [46]
  Ahamad, S.; Kant, R.; Mohanan, K. Org. Lett. 2016, 18, 280. doi: 10.1021/acs.orglett.5b03437
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