Citation: Zhu Lili, Zhang Hui, Wang Chunjie, Chen Zili. Recent Progress in the Synthesis of N²-Substituted 1, 2, 3-Triazoles[J]. Chinese Journal of Organic Chemistry, ;2018, 38(5): 1052-1064. doi: 10.6023/cjoc201710018 shu

Recent Progress in the Synthesis of N²-Substituted 1, 2, 3-Triazoles

Zhu Lili ^a,, ,
Zhang Hui ^a ,
Wang Chunjie ^a ,
Chen Zili ^b,,

a.
School of Chemistry and Chemical Engneering, Zhoukou Normal University, Zhoukou 466001
b.
Department of Chemistry, Renmin University of China, Beijing 100872

Corresponding author: Zhu Lili, lily77cq@163.com Chen Zili, zilichen@ruc.edu.cn
Received Date: 16 December 2017
Revised Date: 20 December 2017
Available Online: 10 May 2018
Fund Project: the Doctoral Scientific Research Foundation of Zhoukou Normal University ZKNUB2013001the Science and Technology Research Program of Henan Province 162300410197Project supported by the National Natural Science Foundation of China (No. 21472237), the Science and Technology Research Program of Henan Province (No. 162300410197), the Scientific Research Innovation Foundation of Zhoukou Normal University (No. ZKNUA201701) and the Doctoral Scientific Research Foundation of Zhoukou Normal University (No. ZKNUB2013001)the Scientific Research Innovation Foundation of Zhoukou Normal University ZKNUA201701the National Natural Science Foundation of China 21472237

Figures(26)

N-Substituted 1, 2, 3-triazole is an important structural unit in organic chemistry, and has widely utilized in organic synthesis, medicinal chemistry and material science. The chemistry of N¹-substituted 1, 2, 3-triazoles has attracted much attention from organic chemists, while the synthesis and application of their N²-isomers have been far less explored. The recent progress on the research field of N²-alkyl, allyl, propargyl, vinyl, aryl substituted 1, 2, 3-triazoles since year 2000 is summarized, including some research of our group. The content is classified by different synthetic methods, such as selective functionalization of 1, 2, 3-triazoles and oxidative cyclization of bisarylhydrazones or azobenzenes.
- 1, 2, 3-triazole,
- selective N²-fuctionalization,
- alkylation,
- allylation,
- propargylation,
- vinylation,
- arylation,
- cyclization
1. [1]
2. [2]
  (a) Huisgen, R. Angew. Chem., Int. Ed. 1963, 2, 565.
  (b) Huisgen, R. 1, 3-Dipolar Cycloaddition Chemistry, Ed. : Padwa, A., Wiley, New York, 1984, pp. 1~176.
3. [3]
  (a) Kolb, H. C. ; Finn, M. G. ; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.
  (b) Rostovtsev, V. V. ; Green, L. G. ; Fokin, V. V. ; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
  (c) Zhang, L. ; Chen, X. ; Xue, P. ; Sun, H. H. Y. ; Williams, I. D. ; Sharpless, K. B. ; Fokin, V. V. ; Jia, G. J. Am. Chem. Soc. 2005, 127, 15998.
  (d) Rasmussen, L. K. ; Boren, B. C. ; Fokin, V. V. Org. Lett. 2007, 9, 5337.
4. [4]
5. [5]
6. [6]
  (a) Mangion, I. K. ; Sherry, B. D. ; Yin, J. ; Fleitz, F. J. Org. Lett. 2012, 14, 3458.
  (b) Adibekian, A. ; Martin, B. R. ; Wang, C. ; Hsu, K. -L. ; Bachovchin, D. A. ; Niessen, S. ; Hoover, H. ; Cravatt, B. F. Nat. Chem. Biol. 2011, 7, 469.
  (c) Cox, C. D. ; Breslin, M. J. ; Whitman, D. B. ; Schreier, J. D. ; McGaughey, G. B. ; Bogusky, M. J. ; Roecker, A. J. ; Mercer, S. P. ; Bednar, R. A. ; Lemaire, W. ; Bruno, J. G. ; Reiss, D. R. ; Harrell, C. M. ; Murphy, K. L. ; Garson, S. L. ; Doran, S. M. ; Prueksaritanont, T. ; Anderson, W. B. ; Tang, C. ; Roller, S. ; Cabalu, T. D. ; Cui, D. ; Hartman, G. D. ; Young, S. D. ; Koblan, K. S. ; Winrow, C. J. ; Renger, J. J. ; Coleman, P. J. J. Med. Chem. 2010, 53, 5320.
  (d) Baxter, C. A. ; Cleator, E. ; Brands, K. M. J. ; Edwards, J. S. ; Reamer, R. A. ; Sheen, F. J. ; Stewart, G. W. ; Strotman, N. A. ; Wallace, D. Org. Process Res. Dev. 2011, 15, 367.
7. [7]
  Chen, Y.; Liu, Y.; Petersena, J. L.; Shi, X. Chem. Commun. 2008, 3254.
8. [8]
  Kalisiak, J.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2008, 10, 3171. doi: 10.1021/ol8006748
9. [9]
  Wang, X.-J.; Sidhu, K.; Zhang, L.; Campbell, S.; Haddad, N.; Reeves, D. C.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2009, 11, 5490. doi: 10.1021/ol902334x
10. [10]
  Wang, X.-J.; Zhang, L.; Krishnamurthy, D.; Senanayake, C. H.; Wipf, P. Org. Lett. 2010, 12, 4632. doi: 10.1021/ol101965a
11. [11]
  Yan, W.; Liao, T.; Tuguldur, O.; Zhong, C.; Petersen, J. L.; Shi, X. Chem.-Asian J. 2011, 6, 2720. doi: 10.1002/asia.v6.10
12. [12]
  Girish, Y. R.; Kumar, K. S. S.; Muddegowda, U.; Lokanath, N. K.; Rangappa, K. S.; Shashikanth, S. RSC Adv. 2014, 4, 55800. doi: 10.1039/C4RA09970B
13. [13]
  Shi, J.; Zhu, L.; Wen, J.; Chen, Z. Chin. J. Catal. 2016, 37, 1222. doi: 10.1016/S1872-2067(15)61107-X
14. [14]
  Jiang, Y.; Wang, Q.; Sun, R.; Tang, X.-Y.; Shi, M. Org. Chem. Front. 2016, 3, 744. doi: 10.1039/C6QO00102E
15. [15]
  Denmark, S. E.; Kuester, W. E.; Burk, M. T. Angew. Chem., Int. Ed. 2012, 51, 10938. doi: 10.1002/anie.201204347
16. [16]
  Zhu, L.-L.; Xu, X.-Q.; Shi, J.-W.; Chen, B.-L.; Chen, Z. J. Org. Chem. 2016, 81, 3568. doi: 10.1021/acs.joc.6b00185
17. [17]
  Wei, H.; Hu, Q.; Ma, Y.; Wei, L.; Liu, J.; Shi, M.; Wang, F. Asian J. Org. Chem. 2017, 6, 662. doi: 10.1002/ajoc.v6.6
18. [18]
  Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 7786. doi: 10.1021/ja034191s
19. [19]
  Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. J. Org. Chem. 2004, 69, 2386. doi: 10.1021/jo035292b
20. [20]
  Xu, K.; Thieme, N.; Breit, B. Angew. Chem., Int. Ed. 2014, 53, 7268. doi: 10.1002/anie.201403682
21. [21]
  Yan, Wu.; Wang, Q.; Chen, Y.; Petersen, J. L.; Shi, X. Org. Lett. 2010, 12, 3308. doi: 10.1021/ol101082v
22. [22]
  Duan, H.; Yan, W.; Sengupta, S.; Shi, X. Bioorg. Med. Chem. Lett. 2009, 19, 3899. doi: 10.1016/j.bmcl.2009.03.096
23. [23]
  Yan, W.; Ye, X.; Weise, K.; Petersen, J. L.; and Shi, X. Chem. Commun. 2012, 48, 3521. doi: 10.1039/c2cc17522c
24. [24]
  Zhang, Z.; Chang, L.; Wang, S.; Wang, H.; Yao, Z.-J. RSC Adv. 2013, 3, 18446. doi: 10.1039/c3ra43075h
25. [25]
  Poznański, J.; Najda, A.; Bretner, M.; Shugar, D. J. Phys. Chem. A 2007, 111, 6501.
26. [26]
  Kitamura, T.; Morshed, M. H.; Tsukada, S.; Miyazaki, Y.; Iguchi, N.; Inoue, D. J. Org. Chem. 2011, 76, 8117. doi: 10.1021/jo2015467
27. [27]
  Liu, Y.; Yan, W.; Chen, Y.; Petersen, J. L.; Shi, X. Org. Lett. 2008, 10, 5389. doi: 10.1021/ol802246q
28. [28]
  Yan, W.; Wang, Q.; Lin, Q.; Li, M.; Petersen, J. L.; Shi, X. Chem.-Eur. J. 2011, 17, 5011. doi: 10.1002/chem.v17.18
29. [29]
  Zhang, Y.; Ye, X.; Petersen, J. L.; Li, M.; Shi, X. J. Org. Chem. 2015, 80, 3664. doi: 10.1021/acs.joc.5b00006
30. [30]
  Wang, X.-J.; Zhang, L.; Lee, H.; Haddad, N.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2009, 11, 5026. doi: 10.1021/ol9019875
31. [31]
  Li, J.; Zhang, Y.; Wang, D.; Wang, W.; Gao, T.; Wang, L.; Li, J.; Huang, G.; Chen, B. Synlett 2010, 1617.
32. [32]
  Liu, X.; Li, J.; Chen, B. New J. Chem. 2013, 37, 965. doi: 10.1039/c3nj40912k
33. [33]
  Zhang, Y.; Li, X.; Li, J.; Chen, J.; Meng, X.; Zhao, M.; Chen, B. Org. Lett. 2012, 14, 26. doi: 10.1021/ol202718d
34. [34]
  Kamal, A.; Swapna, P. RSC Adv. 2013, 3, 7419. doi: 10.1039/c3ra22485f
35. [35]
  Singh, D. P.; Allam, B. K.; Singh, R.; Singh, K. N.; Singh, V. P. RSC Adv. 2016, 6, 15518. doi: 10.1039/C5RA27907K
36. [36]
  Ueda, S.; Su, M.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 8944. doi: 10.1002/anie.v50.38
37. [37]
  Ueda, S.; Ali, S.; Fors, B. P.; Buchwald, S. L. J. Org. Chem. 2012, 77, 2543. doi: 10.1021/jo202537e
38. [38]
  Lopes, A. B.; Wagner, P.; Souza, R. O. M. A.; Germain, N. L.; Uziel, J.; Bourguignon, J.-J.; Schmitt, M.; Miranda, L. S. M. J. Org. Chem. 2016, 81, 4540. doi: 10.1021/acs.joc.6b00323
39. [39]
  Wen, J.; Zhu, L.-L.; Bi, Q.-W.; Shen, Z.-Q.; Li, X.-X.; Li, X.; Wang, Z.; Chen, Z. Chem.-Eur. J. 2014, 20, 974. doi: 10.1002/chem.201302761
40. [40]
  Gu, C.-X.; Bi, Q.-W.; Gao, C.-K.; Wen, J.; Zhao, Z.-G.; Chen, Z. Org. Biomol. Chem. 2017, 15, 3396. doi: 10.1039/C7OB00329C
41. [41]
  Zhang, Y.-C.; Jin, R.; Li, L.-Y.; Chen, Z.; Fu, L.-M. Molecules 2017, 22, 1380. doi: 10.3390/molecules22091380
42. [42]
  Guru, M. M.; Punniyamurthy, T. J. Org. Chem. 2012, 77, 5063. doi: 10.1021/jo300592t
43. [43]
  Stewart, S.; Harris, R.; Jamieson, C. Synlett 2014, 2480.
44. [44]
  Wu, L.; Guo, S.; Wang, X.; Guo, Z.; Yao, G.; Lin, Q.; Wu, M. Tetrahedron Lett. 2015, 56, 2145. doi: 10.1016/j.tetlet.2015.03.019
45. [45]
  Gavlik, K. D.; Lesogorova, S. G.; Sukhorukova, E. S.; Subbotina, J. O.; Slepukhin, P. A.; Benassi, E.; Belskaya, N. P. Eur. J. Org. Chem. 2016, 2700.
46. [46]
  Ai, W. M. S. Thesis, Dalian University of Technology, Dalian, 2008 (in Chinese).
47. [47]
  Liu, G.-B.; Zhao, H.-Y.; Yang, H.-J.; Gao, X.; Li, M.-K.; Thiemannb, T. Adv. Synth. Catal. 2007, 349, 1637. doi: 10.1002/(ISSN)1615-4169
48. [48]
  Dong, J.; Jin, B.; Sun, P. Org. Lett. 2014, 16, 4540. doi: 10.1021/ol502090n
49. [49]
  Zhou, Z.; Liu, Q.-L.; Li, W.; Zhu, Y.-M. Heterocycles 2011, 83, 2057. doi: 10.3987/COM-11-12264
50. [50]
  Kale, R. R.; Prasad, V.; Hussain, H. A.; Tiwari, V. K. Tetrahedron Lett. 2010, 51, 5740. doi: 10.1016/j.tetlet.2010.08.083
51. [51]
  Shang, X.; Zhao, S.; Chen, W.; Chen, C.; Qiu, H. Chem.-Eur. J. 2014, 20, 1825. doi: 10.1002/chem.v20.7
52. [52]
  Liu, Q.-L.; Wen, D.-D.; Hang, C.-C.; Li, Q.-L.; Zhu, Y.-M. Helv. Chim. Acta 2010, 93, 1350. doi: 10.1002/hlca.v93:7
53. [53]
  Zhou, J.; He, J.; Wang, B.; Yang, W.; Ren, H. J. Am. Chem. Soc. 2011, 133, 6868. doi: 10.1021/ja2007438
54. [54]
  Ryu, T.; Min, J.; Choi, W.; Jeon, W. H.; Lee, P. H. Org. Lett. 2014, 16, 2810. doi: 10.1021/ol501250t
55. [55]
  Khatun, N.; Modi, A.; Ali, W.; Patel, B. K. J. Org. Chem. 2015, 80, 9662. doi: 10.1021/acs.joc.5b01706
56. [56]
  Li, J.; Zhou, H.; Zhang, J.; Yang, H.; Jiang, G. Chem. Commun. 2016, 52, 9589. doi: 10.1039/C6CC04341K
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

Recent Progress in the Synthesis of N2-Substituted 1, 2, 3-Triazoles

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通讯作者: 陈斌, bchen63@163.com

Recent Progress in the Synthesis of N²-Substituted 1, 2, 3-Triazoles