5H-[1,2,4]三嗪并[5,6-b]吲哚-3-硫醇类化合物的简便合成  

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

作　　者：高文涛[1] 兰帅[1] 白仁青卓玛 李阳[1] 

机构地区：[1]渤海大学超精细化学品研究所,锦州121000

出　　处：《有机化学》2014年第10期2106-2118,共13页Chinese Journal of Organic Chemistry

基　　金：辽宁省自然科学基金(No.20120001);辽宁省教育厅科学研究(No.L2013428)资助项目~~

摘　　要：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.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.

关 键 词：7-甲(乙)基靛红 5-溴-7-甲(乙)基靛红 溴代 烃基化 5H-[1 2 4]三嗪并[5 6-b]吲哚-3-硫醇 

分 类 号：O626[理学—有机化学]