Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (10): 2106-2118.DOI: 10.6023/cjoc201404014 Previous Articles     Next Articles



高文涛, 兰帅, 白仁青卓玛, 李阳   

  1. 渤海大学超精细化学品研究所 锦州 121000
  • 收稿日期:2014-04-08 修回日期:2014-05-08 发布日期:2014-06-03
  • 通讯作者: 高文涛
  • 基金资助:

    辽宁省自然科学基金(No. 20120001)及辽宁省教育厅科学研究(No. L2013428)资助项目.

Convenient Synthesis 5H-[1,2,4]Triazine[5,6-b]indole-3-thiol Derivatives

Gao Wentao, Lan Shuai, Bairenqing Zhuoma, Li Yang   

  1. Institute of Superfine Chemicals, Bohai University, Jinzhou 121000
  • Received:2014-04-08 Revised:2014-05-08 Published:2014-06-03
  • Supported by:

    Project supported by the Natural Science Foundation of Liaoning Province (No. 20120201) and the Scinetific Research Foundation of the Education Department of Liaoning Province (No. L1013428).

2-Methyl(ethyl)aniline 1a, 1b were first underwent the Sandmeyer reaction to give 7-methyl (ethyl) isatins 2a, 2b. The resulting 2a, 2b were then subjected to the bromination reaction with N-bromosuccinimide (NBS) using eco-friendly PEG-400 as solvent at room temperature to afford 5-bromo-7-methyl (ethyl) isatins 3a, 3b. Compounds 2a, 2b, 3a, 3b were further alkylated at the nitrogen atom to give the corresponding 1-alkylation-7-methyl (ethyl) isatins 4a4j, and 1-alkylation-5-bromo-7-methyl(ethyl)isatins 5a5j. Finally, 2a, 2b, 3a, 3b, 4a4j, 5a5j were subjected to the condensation reaction with thiosemicarbazide using dioxane as solvent and potassium carbonate as alkali to successfully synthesize 24 kinds of 5H-[1,2,4]triazine[5,6-b]indole-3-thiol derivatives 6a6x. Most of compounds were new and their structures were confirmed by IR, MS, 1H NMR and 13C NMR spectra and elemental analyses.

Key words: 7-methyl(ethyl)isatin, 5-bromo-7-methyl(ethyl)isatin, bromination, alkylation, 5H-[1,2,4]triazino-[5,6-b]-indole-3-thiol