5H-[1,2,4]三嗪并[5,6-b]吲哚-3-硫醇类化合物的简便合成
收稿日期: 2014-04-08
修回日期: 2014-05-08
网络出版日期: 2014-06-03
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
Received date: 2014-04-08
Revised date: 2014-05-08
Online 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).
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、核磁氢谱（碳谱）和元素分析确认.
高文涛 , 兰帅 , 白仁青卓玛 , 李阳 . 5H-[1,2,4]三嗪并[5,6-b]吲哚-3-硫醇类化合物的简便合成[J]. 有机化学, 2014 , 34(10) : 2106 -2118 . DOI: 10.6023/cjoc201404014
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 4a～4j, and 1-alkylation-5-bromo-7-methyl(ethyl)isatins 5a～5j. Finally, 2a, 2b, 3a, 3b, 4a～4j, 5a～5j 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.
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