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
收稿日期: 2014-03-25
修回日期: 2014-04-17
网络出版日期: 2014-05-06
基金资助
国家自然科学基金(No. 20272008)和鞍山市科技基金(Nos. 2011MS44 和 2012KJ02)资助项目.
Selective Synthesis of 3-(3-Indolyl)-3-(methylthio)acrylate and 3-(3-Indolyl)-3-oxopropanoate
Received date: 2014-03-25
Revised date: 2014-04-17
Online published: 2014-05-06
Supported by
Project supported by the National Natural Science Foundation of China (No. 20272008) and the Science Foundation of Anshan City (Nos. 2011MS44, 2012KJ02).
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
于海丰 , 廖沛球 , 刁全平 , 李铁纯 , 辛广 , 韩立楠 , 侯冬岩 . 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[J]. 有机化学, 2014 , 34(9) : 1851 -1856 . DOI: 10.6023/cjoc201403055
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 the silica gel. This transformation is characterized by mild reaction conditions, simple procedure, good yield, and perfect selectivity.
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