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

Figures(54)

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
1. [1]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
2. [2]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
3. [3]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
4. [4]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
5. [5]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
6. [6]
  Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C₃N₄/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
7. [7]
  Jianyu Qin , Yuejiao An , Yanfeng Zhang . In Situ Assembled ZnWO₄/g-C₃N₄ S-Scheme Heterojunction with Nitrogen Defect for CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408002-. doi: 10.3866/PKU.WHXB202408002
8. [8]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
9. [9]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
10. [10]
  Qianqian Liu , Xing Du , Wanfei Li , Wei-Lin Dai , Bo Liu . Synergistic Effects of Internal Electric and Dipole Fields in SnNb₂O₆/Nitrogen-Enriched C₃N₅ S-Scheme Heterojunction for Boosting Photocatalytic Performance. Acta Physico-Chimica Sinica, 2024, 40(10): 2311016-. doi: 10.3866/PKU.WHXB202311016
11. [11]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
12. [12]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
13. [13]
  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
14. [14]
  Jinyi Sun , Lin Ma , Yanjie Xi , Jing Wang . Preparation and Electrocatalytic Nitrogen Reduction Performance Study of Vanadium Nitride@Nitrogen-Doped Carbon Composite Nanomaterials: A Recommended Comprehensive Chemistry Experiment. University Chemistry, 2024, 39(4): 184-191. doi: 10.3866/PKU.DXHX202310094
15. [15]
  Kaihui Huang , Dejun Chen , Xin Zhang , Rongchen Shen , Peng Zhang , Difa Xu , Xin Li . Constructing Covalent Triazine Frameworks/N-Doped Carbon-Coated Cu₂O S-Scheme Heterojunctions for Boosting Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(12): 2407020-. doi: 10.3866/PKU.WHXB202407020
16. [16]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
17. [17]
  Hailang JIA , Hongcheng LI , Pengcheng JI , Yang TENG , Mingyun GUAN . Preparation and performance of N-doped carbon nanotubes composite Co₃O₄ as oxygen reduction reaction electrocatalysts. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 693-700. doi: 10.11862/CJIC.20230402
18. [18]
  Cuiwu MO , Gangmin ZHANG , Chao WU , Zhipeng HUANG , Chi ZHANG . A(NH₂SO₃) (A=Li, Na): Two ultraviolet transparent sulfamates exhibiting second harmonic generation response. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1387-1396. doi: 10.11862/CJIC.20240045
19. [19]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
20. [20]
  Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246

Get Citation

PDF

XML

Metrics

PDF Downloads(460)
Abstract views(9296)
HTML views(3356)

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