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

DOI: 10.6023/cjoc201404014 研究论文 有机化学 Chinese Journal of Organic Chemistry ARTICLE 5H-[1,2,4]三嗪并[5,6-b]吲哚-3-硫醇类化合物的简便合成 高文涛* 兰 帅 白仁青卓玛 李 阳 (渤海大学超精细化学品研究所 锦州 121000) 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. 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 Convenient Synthesis 5H-[1,2,4]Triazine[5,6-b]indole-3-thiol Deriva- tives Gao, Wentao* Lan, Shuai Bairenqing, Zhuoma Li, Yang (Institute of Superfine Chemicals, Bohai University, Jinzhou 121000) Abstract 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 condensa- tion reaction