Citation: Liu Jiangong, Li Xiaolong, Cheng Xu, Hao Wenmei, Hai Li, Wu Yong. Condensation of 1-(1-Ethyl-1H-indol-5-yl)-2-phenylethane- 1,2-dione to 1,2,4-Triazines[J]. Chinese Journal of Organic Chemistry, ;2016, 36(2): 370-376. doi: 10.6023/cjoc201509010 shu

Condensation of 1-(1-Ethyl-1H-indol-5-yl)-2-phenylethane- 1,2-dione to 1,2,4-Triazines

1.
West China School of Pharmacy, Sichuan University, Chengdu 610041

Corresponding author: Wu Yong,
Received Date: 8 September 2015
Available Online: 6 October 2015

This paper reports the selective condensation of aminoguanidine with 1-(1-ethyl-1H-indol-5-yl)-2-phenylethane- 1,2-dione to afford 1,2,4-triazines. The constituents and relative proportion of these condensation products are identified by the methods of target-oriented synthesis and nuclear magnetic resonance. And the influences on the relative proportion by different substituents are described. When the phenyl is substituted with the electron-withdrawing group, the ratio of the isomers 6-(1-ethyl-1H-indol-5-yl)-5-phenyl-1,2,4-triazin-3-amine/5-(1-ethyl-1H-indol-5-yl)-6-phenyl-1,2,4-triazin-3-amine [n(2a):n(4a)] is 40:60; when without the substituent, the ratio of the isomers 6-(1-ethyl-1H-indol-5-yl)-5-(4-nitrophenyl)- 1,2,4-triazin-3-amine/5-(1-ethyl-1H-indol-5-yl)-6-(4-nitrophenyl)-1,2,4-triazin-3-amine [n(2b):n(4b)] is 63:37; when substituted with the electron-donating group, the type of the major products was 2.
- condensation,
- unsymmetrical 1,2-diketone,
- isomer,
- 1,2,4-triazine
1. [1]
  [1] Lu, Z.-E.; Wan, J.; Chen, K. Q. Chin. J. Org. Chem. 1992, 12, 605 (in Chinese). (陆忠娥, 万军, 陈克潜, 有机化学, 1992, 12, 605.)
2. [2]
  [2] Li, Y. J.; Shao, X.; Gao, L. X.; Jin, K.; Sheng, L.; Luo, T. C.; Yu, Y.; Li, J. Chin. J. Org. Chem. 2013, 33, 2178 (in Chinese). (李英俊, 邵昕, 高立信, 靳焜, 盛丽, 罗潼川, 于洋, 李佳, 有机化学, 2013, 33, 2178.)
3. [3]
  [3] Li, Y. J.; Shi, X. L.; Gao, L. X.; Jin, K.; Sheng, L.; Wu, J. H.; Peng, L. N.; Li, J. Chin. J. Org. Chem. 2015, 35, 191 (in Chinese). (李英俊, 史相玲, 高立信, 靳焜, 盛丽, 吴疆红, 彭立娜, 李佳, 有机化学, 2015, 35, 191.)
4. [4]
  [4] Eid, M. M.; Mansour, A. K. J. Heterocycl. Chem. 1988, 25, 1139.
5. [5]
  [5] Rees, R. W. A.; Russell, P. B.; Foell, T. J.; Bright, R. E. J. Med. Chem. 1972, 15, 859.
6. [6]
  [6] March, L. C.; Bajwa, G. S.; Lee, J.; Wasti, K.; Joullie, M. M. J. Med. Chem. 1976, 19, 845.
7. [7]
  [7] Kim, J. W.; Lee, D. Y.; Park, C. M. ACS Med. Chem. Lett. 2012, 3, 678.
8. [8]
  [8] Congreve, M.; Andrews, S. P.; Dore, A. S.; Hollenstein, K. J. Med. Chem. 2012, 55, 1898.
9. [9]
  [9] Xie, F. C.; Zhao, H. B.; Li, D. W.; Chen, H.; Quan, H. T.; Shi, X. J.; Lou, L. G.; Hu, Y. H. J. Med. Chem. 2011, 54, 3200.
10. [10]
  [10] Mallikarjuna, B. P.; Suresh, K. G. V.; Sastry, B. S.; Nagaraj; Manohara, K. P. J. Zhejiang Univ., Sci. B 2007, 8, 526.
11. [11]
  [11] Cheng, X.; Li, X. L.; Wan, W. L.; Hao, W. M.; Hai, L.; Wu, Y. Chem. Res. Chin. Univ. 2015, 31, 53.
12. [12]
  [12] Congreve, M.; Andrews, S. P.; Mason, J. S.; Richardson, C. M.; Brown, G. A. WO 2011095625, 2011 [Chem. Abstr. 2011, 155, 271296].
1. [1]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
2. [2]
  Renqing Lü , Shutao Wang , Fang Wang , Guoping Shen . Computational Chemistry Aided Organic Chemistry Teaching: A Case of Comparison of Basicity and Stability of Diazine Isomers. University Chemistry, 2025, 40(3): 76-82. doi: 10.12461/PKU.DXHX202404119
3. [3]
  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
4. [4]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
5. [5]
  Tong Wang , Liangyu Hu , Shiqi Chen , Xinqiang Fu , Rui Wang , Kun Li , Shuangyan Huan . Determination of Benzenediol Isomers in Cosmetics Using High-Performance Liquid Chromatography Empowered by “Mathematical Separation”. University Chemistry, 2026, 41(1): 9-19. doi: 10.12461/PKU.DXHX202503128
6. [6]
  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
7. [7]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
8. [8]
  Xiyuan Zhang , Rui Dong , Yang Yang , Jiapeng Ding , Zhiwei Miao . Palladium-Catalyzed Tandem Cyclization of 4-Vinylbenzoxazinone and Indene-2-carbaldehyde: A Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(9): 361-367. doi: 10.12461/PKU.DXHX202410062
9. [9]
  Shiqi Xu , Zi Ye , Shuang Shang , Fengge Wang , Huan Zhang , Lianguo Chen , Hao Lin , Chen Chen , Fang Hua , Chong-Jing Zhang . Pairs of thiol-substituted 1,2,4-triazole-based isomeric covalent inhibitors with tunable reactivity and selectivity. Chinese Chemical Letters, 2024, 35(7): 109034-. doi: 10.1016/j.cclet.2023.109034
10. [10]
  Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
11. [11]
  Jianquan Liu , Xiangshan Wang . Teaching Design and Practice of Naming Rules for Circular Isomer Configuration under the Guidance of Information Literacy. University Chemistry, 2025, 40(7): 352-358. doi: 10.12461/PKU.DXHX202409082
12. [12]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
13. [13]
  Guoxi Yang , Hongji Tan , Jieji Zhu , Qingxiao Tong , Jingxin Jian , Zhihai Yang , Deli Li , Denghui Liu , Shijian Su . [1,2,4]Triazolo[1,5-a]pyridine as regulating unit with high horizontal orientation for efficient non-doped blue OLEDs with negligible efficiency roll-off. Chinese Chemical Letters, 2025, 36(8): 111138-. doi: 10.1016/j.cclet.2025.111138
14. [14]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
15. [15]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
16. [16]
  Xiaolei Jiang , Fangdong Hu . Exploring the Mirror World in Organic Chemistry: the Teaching Design of “Enantiomers” from the Perspective of Curriculum and Ideological Education. University Chemistry, 2024, 39(10): 174-181. doi: 10.3866/PKU.DXHX202402052
17. [17]
  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
18. [18]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
19. [19]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
20. [20]
  Xiaochun Liu , Gaoyan Chen , Xiaodong Yue , Chaoyue Wang , Xue-Xin Zhang , Xuecheng Ran , Yingxiao Zong , Junke Wang , Xicun Wang . A novel N-stable Co₂P nano-catalyst for the synthesis of quinoxalines by annulation of alkynes and 1,2-diaminobenzenes. Chinese Chemical Letters, 2025, 36(8): 110707-. doi: 10.1016/j.cclet.2024.110707

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(1356)
HTML views(161)

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