Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (2): 370-376.DOI: 10.6023/cjoc201509010 Previous Articles     Next Articles



刘剑功, 黎晓龙, 程旭, 郝文梅, 海俐, 吴勇   

  1. 四川大学华西药学院 成都 610041
  • 收稿日期:2015-09-08 修回日期:2015-10-06 发布日期:2015-10-13
  • 通讯作者: 吴勇

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

Liu Jiangong, Li Xiaolong, Cheng Xu, Hao Wenmei, Hai Li, Wu Yong   

  1. West China School of Pharmacy, Sichuan University, Chengdu 610041
  • Received:2015-09-08 Revised:2015-10-06 Published:2015-10-13

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.

Key words: condensation, unsymmetrical 1,2-diketone, isomer, 1,2,4-triazine