3-吲哚基-3-甲硫基丙烯酸酯和3-吲哚基-3-氧代丙酸酯的选择性合成有机化学.pdfVIP

DOI: 10.6023/cjoc201403055 研究论文 有机化学 Chinese Journal of Organic Chemistry ARTICLE 3-吲哚基-3- 甲硫基丙烯酸酯和3-吲哚基-3-氧代丙酸酯的选择性合成 于海丰*,a 廖沛球b 刁全平a 李铁纯a 辛 广a 韩立楠a 侯冬岩*,a a ( 鞍山师范学院化学与生命科学学院 鞍山 114007) (b 东北师范大学化学学院 长春 130024) 摘要 在 10 ℃, 3,3-二甲硫基丙烯酸酯、吲哚和三氟乙酸(TFA)的物质的量之比为 1 ∶1 ∶15 时, 研究了 3,3-二甲硫基丙 烯酸酯的吲哚化反应. 通过控制产物在硅胶的停留时间选择性制备了 3-吲哚基-3- 甲硫基丙烯酸酯(83%～85%)和 3-吲 哚基-3-氧代丙酸酯(83%～89%). 反应条件温和、操作简单、产率高且选择性好. 关键词 α-羰基二硫缩烯酮; 3-吲哚基-3-烷硫基丙烯酸酯; 3-吲哚基-3-氧代丙酸酯; 吲哚衍生物; 选择性合成 Selective Synthesis of 3-(3-Indolyl)-3-(methylthio)acrylate and 3-(3-Indolyl)-3-oxopropanoate Yu, Haifeng*,a Liao, Peiqiub Diao, Quanpinga Li, Tiechuna Xin, Guanga Han, Linana Hou, Dongyan*,a a ( School of Chemistry and Life Science, Anshan Normal University, Anshan 114007) b ( Department of Chemistry, Northeast Normal University, Changchun 130024) Abstract The indolylation reaction of 3,3-bis(methylthio)acrylates was performed at 10 ℃ when the molar ratio of 3,3-bis(methylthio)acrylates, indoles and trifluoroacetic acid (TFA) was 1 ∶1 ∶15. It showed that 3-(3-indolyl)-3-(methyl- thio)acrylate and 3-(3-indolyl)-3-oxopropanoate could be selectively obtained in excellent yield by controlling the detention time of 3-(3-indolyl)-3-(methylthio)acrylate in th