Citation: Li Mingrui, Ding Qifeng, Li Boyang, Yu Yang, Huang He, Huang Fei. Progress in the Synthesis of 1, 2, 4-Triazines by Tandem Cyclization[J]. Chinese Journal of Organic Chemistry, ;2019, 39(10): 2713-2725. doi: 10.6023/cjoc201905036 shu

Progress in the Synthesis of 1, 2, 4-Triazines by Tandem Cyclization

Li Mingrui ^a ,
Ding Qifeng ^a ,
Li Boyang ^a ,
Yu Yang ^c ,
Huang He ^a,b ,
Huang Fei ^a,b,,

a.
School of Pharmaceutical Sciences, Nanjing Tech University, Nanjing 211816
b.
School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, Nanjing 210023
c.
School of Environmental and Engineering, Nanjing Tech University, Nanjing 211816

Corresponding author: Huang Fei, huangfei0208@yeah.net
Received Date: 14 May 2019
Revised Date: 3 June 2019
Available Online: 24 October 2019
Fund Project: the National Natural Science Foundation of China 21901124the Jiangsu Synergetic Innovation Center for Advanced Bio-Manufacture XTE1850Project supported by the National Natural Science Foundation of China (No. 21901124), the Jiangsu University Natural Science Research Program (No. 19KJB150032), the China Postdoctoral Science Foundation (No. 2019M651809), the Jiangsu Synergetic Innovation Center for Advanced Bio-Manufacture (No. XTE1850) and the Postdoctoral Science Foundation of Anhui Province (No. 2018B252)the Jiangsu University Natural Science Research Program 19KJB150032the China Postdoctoral Science Foundation 2019M651809the Postdoctoral Science Foundation of Anhui Province 2018B252

Figures(25)

1, 2, 4-Triazine compounds are an important class of nitrogen-containing heterocyclic compounds. They have wide applications in the fields of medicine, chemicals and materials. Therefore, green and highly efficient synthesis of 1, 2, 4-triazine compounds is increasingly attracting the attention of researchers. By tandem cyclization reaction, the post-treatment of intermediate is avoided, and the one-pot synthesis of triazine compounds is the most efficient and direct synthesis method, which conforms to the concept of green chemistry for its step and atomic economy. The formation of C-N bond based on tandem cyclization to give 1, 2, 4-triazine compounds is reviewed. The synthetic method, reaction mechanism and application of 1, 2, 4-triazine compounds are introduced under transition-metal and metal-free conditions in the past ten years. The prospects of synthesis of triazine rings are also discussed.
- 1, 2, 4-triazine,
- tandem cyclization,
- C-N bond formation,
- transition-metal catalysis,
- metal-free catalysis
1. [1]
  (a) Majumdar, P.; Pati, A.; Patra, M.; Behera, R. K.; Behera, A. K. Chem. Rev. 2014, 114, 2942.
  (b) Kelly, T. R.; Elliott, E. L.; Lebedev, R.; Pagalday, J. J. Am. Chem. Soc. 2006, 128, 5646.
  (c) Blair, L. M.; Sperry, J. J. Nat. Prod. 2013, 76, 794.
2. [2]
3. [3]
  (a) Patrizia, D.; Annamaria, M.; Paola, B.; Antonino, L.; Alessandra, M.; Anna, M. A.; Gaetano, D.; Girolamo, C. Bioorg. Med. Chem. 2007, 15, 343.
  (b) Tomas, G.; Eva, R.; Petr, D.; Marian, H.; Vladimir, K. Monatsh. Chem. 2010, 141, 709.
  (c) Jaiprakash, N. S.; Devanand, B. S. Bioorg. Med. Chem. Lett. 2010, 20, 742.
  (d) Badran, M. M.; Ismail, M. A. H.; Abdu, N.; Abdel-Hakeem, M. Alexandria J. Pharm. Sci. 1999, 13, 101.
  (e) Thiele, K.; Gordon, C. J. S.; Fischer, J.; Jahn, U. EP 28660, 1981.
  (f) Messmer, A.; Batori, S.; Hajos, G.; Benko, P. US 4602018, 1986.
  (g) Kelly, T. R.; Elliott, E. L.; Lebedev, R.; Pagalday, J. J. Am. Chem. Soc. 2006, 128, 5646.
4. [4]
  Solaleh, K. T.; Niloufar, A.; Mohsen, A. Apoptosis 2010, 15, 738. doi: 10.1007/s10495-010-0496-6
5. [5]
6. [6]
  (a) Hay, M. P.; Hicks, K. O.; Pchalek, K.; Lee, H. H.; Blaser, A.; Pruijn, F. B.; Anderson, R. F.; Shinde, S. S.; Wilson, W. R.; Denny, W. A. J. Med. Chem. 2008, 51, 6853.
  (b) Vaithianathan, S.; Raman, S.; Jiang, W. L.; Ting, T. Y.; Kane, M. A.; Polli, J. E. Mol. Pharmaceutics 2015, 12, 2436.
  (c) Lojanapiwat, B.; Nimitvilai, S.; Bamroongya, M.; Jirajariyavej, S.; Tiradechavat, C.; Malithong, A.; Predanon, C.; Tanphaichitra, D.; Lertsupphakul, B. Infect. Drug Resist. 2019, 12, 173.
7. [7]
  Suzuki, H.; Kawakami, T. Synthesis 1997, 855.
8. [8]
  Baxter, M. G; Elphick, A. R.; Miller, A. A. US 4486354, 1984.
9. [9]
  Zhang, P.; Wang, J. J.; Xiao, H.; Jiang, Y.; Jiang, X. M. CN 103539803, 2014.
10. [10]
  (a) Dowling, M. S.; Jiao, W. H.; Hou, J.; Jiang, Y. C.; Gong, S. S. J. Org. Chem. 2018, 83, 4229.
  (b) Rätz, R.; Schroeder, H. J. Org. Chem. 1958, 23, 1931.
  (c) Saraswathi, T. V.; Srinivasan, V. R. Tetrahedron Lett. 1971, 12, 2315.
  (d) Kozhevnikov, V. N.; Kozhevnikov, D. N.; Shabunina, O. V.; Rusinov, V. L.; Chupakhin, O. N. Tetrahedron Lett. 2005, 46, 1791.
11. [11]
  (a) Park, Y.; Kim, Y.; Chang, S. Chem. Rev. 2017, 117, 9247
  (b) Dydio, P.; Key, H. M.; Hayashi, H. J. Am. Chem. Soc. 2017, 139, 1750.
  (c) Timsina, Y. N.; Gupton, B. F.; Ellis, K. C. ACS Catal. 2018, 8, 5732.
  (d) Wang, P.; Li, G. C.; Jain, P. J. Am. Chem. Soc. 2016, 138, 14092.
12. [12]
  Liu, L.; Tan, C.; Fan, R.; Wang, Z. H.; Du, H. G.; Xu, K.; Tan, J. J. Org. Biomol. Chem. 2019, 17, 252. doi: 10.1039/C8OB02826E
13. [13]
  Walsh, P. J.; Deng, G. G.; Li, M. Y.; Yu, K. L.; Liu, C. X.; Liu, Z. F.; Duan, S. Z.; Chen, W.; Yang, X. D.; Zhang, H. B. Angew. Chem., Int. Ed. 2019, 58, 2826. doi: 10.1002/anie.201812369
14. [14]
  Wang, J. N.; Chen, S. Q.; Liu, Z. W. J. Org. Chem. 2019, 84, 1348. doi: 10.1021/acs.joc.8b02820
15. [15]
  Rodionov, V. O.; Fokin, V. V.; Finn, M. G. Angew. Chem., Int. Ed. 2005, 117, 2250. doi: 10.1002/ange.200461496
16. [16]
  Guo, H. C.; Liu, H. L.; Zhu, F. L.; Na, R.; Jiang, H.; Wu, Y.; Zhang, L.; Li, Z.; Yu, H.; Wang, B.; Xiao, Y.; Hu, X. P.; Wang, M. Angew. Chem., Int. Ed. 2013, 52, 12641. doi: 10.1002/anie.201307317
17. [17]
  Adrio, J.; Carretero, J. C. Chem. Commun. 2011, 47, 6784. doi: 10.1039/c1cc10779h
18. [18]
  Du, J.; Xu, X.; Li, Y.; Pan, L.; Liu, Q. Org. Lett. 2014, 16, 4004. doi: 10.1021/ol501829k
19. [19]
  Cheng, X.; Cao, X.; Xuan, J.; Xiao, W. J. Org. Lett. 2018, 20, 52. doi: 10.1021/acs.orglett.7b03344
20. [20]
  Chen, Z.; Ren, N.; Ma, X. X.; Nie, J.; Zhang, F. G.; Ma, J. A. ACS Catal. 2019, 9, 4600. doi: 10.1021/acscatal.9b00846
21. [21]
  Hong, D.; Lin, X. F.; Zhu, Y. X.; Lei, M.; Wang, Y. G. Org. Lett. 2009, 11, 5678. doi: 10.1021/ol902376w
22. [22]
  Shi, B.; Lewis, W.; Campbell, I. B.; Moody, C. J. Org. Lett. 2009, 11, 3686. doi: 10.1021/ol901502u
23. [23]
  Wu, W.; Wang, J.; Wang, Y.; Huang, Y.; Tan, Y.; Weng, Z. Q. Angew. Chem., Int. Ed. 2017, 56, 10476. doi: 10.1002/anie.201705620
24. [24]
  Lin, B.; Wu, W.; Weng, Z. Q Tetrahedron 2019, 75, 2843. doi: 10.1016/j.tet.2019.04.005
25. [25]
  Meng, J.; Wen, M.; Zhang, S.; Pan, P.; Yu, X.; Deng, W. P. J. Org. Chem. 2017, 82, 1676. doi: 10.1021/acs.joc.6b02846
26. [26]
  Tang, D.; Wang, J.; Wu, P.; Guo, X.; Li, J. H.; Yang, S.; Chen, B. H. RSC Adv. 2016, 6, 12514. doi: 10.1039/C5RA26638F
27. [27]
  Zhang, L.; Chen, J. J.; Liu, S. S.; Liang, Y. X.; Zhao, Y. L. Adv. Synth. Catal. 2018, 360, 2172. doi: 10.1002/adsc.201800030
28. [28]
  Bigot, A.; Blythe, J.; Pandya, C.; Wagner, T.; Loiseleur, O. Org. Lett. 2010, 13, 192.
29. [29]
  Crespin, L.; Biancalana, L.; Morack, T.; Blakemore, D. C.; Ley, S. V. Org. Lett. 2017, 19, 1084. doi: 10.1021/acs.orglett.7b00101
30. [30]
  Karthikeyan, M. S.; Mahalinga, M.; Karegoundar, P.; Poojary, B.; Holla, B. S. Phosphorus, Sulfur Silicon Relat. Elem. 2009, 184, 3231. doi: 10.1080/10426500902979917
31. [31]
  Tamboli, R. S.; Giridhar, R.; Mande, H. M.; Shah, S. R.; Yadav, M. R. Synth. Commum. 2014, 44, 2192. doi: 10.1080/00397911.2014.891040
32. [32]
  Ghorbani-Vaghei, R.; Shahriari, A.; Salimi, Z.; Hajinazari, S. RSC Adv. 2015, 5, 3665. doi: 10.1039/C4RA10892B
33. [33]
  Savva, A. C.; Mirallai, S. I.; Zissimou, G. A.; Berezin, A. A.; Demetriades, M.; Kourtellaris, A.; Constantinides, C. P.; Nicolaides, C.; Trypiniotis, T, ; Koutentis, P. A. J. Org. Chem. 2017, 82, 7564. doi: 10.1021/acs.joc.7b01297
34. [34]
  Palacios, F.; Alonso, C.; Aparicio, D.; Rubiales, G.; Jesús, M. Tetrahedron 2007, 63, 523. doi: 10.1016/j.tet.2006.09.048
1. [1]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
2. [2]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
3. [3]
  Yanhui Guo , Li Wei , Zhonglin Wen , Chaorong Qi , Huanfeng Jiang . Recent Progress on Conversion of Carbon Dioxide into Carbamates. Acta Physico-Chimica Sinica, 2024, 40(4): 2307004-0. doi: 10.3866/PKU.WHXB202307004
4. [4]
  Lu Zhuoran , Li Shengkai , Lu Yuxuan , Wang Shuangyin , Zou Yuqin . Cleavage of C―C Bonds for Biomass Upgrading on Transition Metal Electrocatalysts. Acta Physico-Chimica Sinica, 2024, 40(4): 2306003-0. doi: 10.3866/PKU.WHXB202306003
5. [5]
  Huiwei Ding , Bo Peng , Zhihao Wang , Qiaofeng Han . Advances in Metal or Nonmetal Modification of Bismuth-Based Photocatalysts. Acta Physico-Chimica Sinica, 2024, 40(4): 2305048-0. doi: 10.3866/PKU.WHXB202305048
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]
  Pengzi Wang , Wenjing Xiao , Jiarong Chen . Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction. University Chemistry, 2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090
8. [8]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
9. [9]
  Fei Xie , Chengcheng Yuan , Haiyan Tan , Alireza Z. Moshfegh , Bicheng Zhu , Jiaguo Yu . d-Band Center Regulated O₂ Adsorption on Transition Metal Single Atoms Loaded COF: A DFT Study. Acta Physico-Chimica Sinica, 2024, 40(11): 2407013-0. doi: 10.3866/PKU.WHXB202407013
10. [10]
  Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO₂ Reduction by Modified g-C₃N₄. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-0. doi: 10.3866/PKU.WHXB202408005
11. [11]
  Qi Wu , Changhua Wang , Yingying Li , Xintong Zhang . Enhanced photocatalytic synthesis of H₂O₂ by triplet electron transfer at g-C₃N₄@BN van der Waals heterojunction interface. Acta Physico-Chimica Sinica, 2025, 41(9): 100107-0. doi: 10.1016/j.actphy.2025.100107
12. [12]
  Xinlong XU , Chunxue JING , Yuzhen CHEN . Bimetallic MOF-74 and derivatives: Fabrication and efficient electrocatalytic biomass conversion. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1545-1554. doi: 10.11862/CJIC.20250046
13. [13]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
14. [14]
  Haitao Wang , Lianglang Yu , Jizhou Jiang , Arramel , Jing Zou . S-Doping of the N-Sites of g-C₃N₄ to Enhance Photocatalytic H₂ Evolution Activity. Acta Physico-Chimica Sinica, 2024, 40(5): 2305047-0. doi: 10.3866/PKU.WHXB202305047
15. [15]
  Xichen YAO , Shuxian WANG , Yun WANG , Cheng WANG , Chuang ZHANG . Oxygen reduction performance of self?supported Fe/N/C three-dimensional aerogel catalyst layers. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1387-1396. doi: 10.11862/CJIC.20240384
16. [16]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . Molten Intermediate Transportation-Oriented Synthesis of Amino-Rich g-C₃N₄ Nanosheets for Efficient Photocatalytic H₂O₂ Production. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-0. doi: 10.3866/PKU.WHXB202406021
17. [17]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . Simultaneously Improving Inter-Plane Crystallization and Incorporating K Atoms in g-C₃N₄ Photocatalyst for Highly-Efficient H₂O₂ Photosynthesis. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-0. doi: 10.3866/PKU.WHXB202406005
18. [18]
  Yan Qi , Yueqin Yu , Weisi Guo , Yongjun Liu . 过渡金属参与的有机反应案例教学与实践探索. University Chemistry, 2025, 40(6): 111-117. doi: 10.12461/PKU.DXHX202411021
19. [19]
  Ruizhi Duan , Xiaomei Wang , Panwang Zhou , Yang Liu , Can Li . The role of hydroxyl species in the alkaline hydrogen evolution reaction over transition metal surfaces. Acta Physico-Chimica Sinica, 2025, 41(9): 100111-0. doi: 10.1016/j.actphy.2025.100111
20. [20]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . Construction of 4-Amino-1H-imidazole-5-carbonitrile Modified Carbon Nitride-Based Donor-Acceptor Photocatalyst for Efficient Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-0. doi: 10.3866/PKU.WHXB202406026

Get Citation

PDF

XML

Metrics

PDF Downloads(46)
Abstract views(4432)
HTML views(1407)

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