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
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沈阳化工大学材料科学与工程学院沈阳 110142