报道了以2-甲(乙)基苯胺1a,1b为原料经Sandmeyer反应得到7-甲(乙)基靛红2a,2b;再以环境友好的聚乙二醇-400为溶剂,N-溴代丁二酰亚胺(NBS)为绿色溴代试剂对2a,2b进行5位溴代,得到5-溴-7-甲(乙)基靛红3a,3b;2a,2b,3a,3b进一步氮烃基化得到1-烃基-7-甲(乙)基靛红4a~4j和1-烃基-5-溴-7-甲(乙)基靛红5a~5j.2a,2b,3a,3b,4a~4j,5a~5j分别与硫代氨基脲,在以二氧六环为溶剂,碳酸钾存在的条件下回流反应,简便地合成了24种5H-[1,2,4]三嗪并[5,6-b]吲哚-3-硫醇类杂环化合物6a~6x.大部分化合物未见文献报道,其结构经红外光谱、质谱、核磁氢辫(碳谱1和儿素分析确认.
2-Methyl(ethyl)aniline la, lb 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 4a~ 4j, and 1-alkylation-5-bromo-7-methyl(ethyl)isatins 5a~Sj. Finally, 2a, 2b, 3a, 3b, 4a~4j, 5a~Sj 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 6a~6x. Most of compounds were new and their structures were confirmed by IR, MS, ^1H NMR and ^13C NMR spectra and elemental analyses.