4,5-二甲基-2-三甲基硅基噻吩-3-甲酰胺衍生物的合成新方法
收稿日期: 2014-06-06
修回日期: 2014-06-20
网络出版日期: 2014-07-03
基金资助
国家“十二五”粮食丰产科技工程(Nos.2011BAD16B07, 2012BAD04B07)及中国科学院现代农业示范和区域创新集群计划(No.CXJQ120111)资助项目.
A New Procedure for Synthesizing 4,5-Dimethyl-2-(trimethylsilyl)-thiophene-3-carboxamide Derivatives
Received date: 2014-06-06
Revised date: 2014-06-20
Online published: 2014-07-03
Supported by
Project supported by the National Food Production Technology Project of China during the Twelfth Five-Year Period (Nos.2011BAD16B07, 2012BAD04B07), and the Modern Agriculture Demonstration and Regional Innovation Cluster Plan Project of the Chinese Academy of Sciences (No.CXJQ120111).
靳文波 , 谢桂英 , 孙淑君 , 赵艳芹 , 程绎南 , 孙炳剑 , 李洪连 . 4,5-二甲基-2-三甲基硅基噻吩-3-甲酰胺衍生物的合成新方法[J]. 有机化学, 2014 , 34(11) : 2376 -2381 . DOI: 10.6023/cjoc201406006
A new procedure for synthesizing 4,5-dimethyl-2-(trimethylsilyl)thiophene-3-carboxamide derivatives was explored. Using commercially available 3-mercaptobutan-2-one and methyl propiolate as starting materials, the target compounds were obtained in four steps via silylanization of methyl propiolate, cyclization, selective hydrolysis and amidation. And the promoters involved in silylanization, cyclization and selective hydrolysis were screened. The procedure exhibited several advantages such as easily available raw materials, mild reaction conditions, easily purified intermediates and high single-step yields. It had potential to be applied to scale production.
Key words： silylanization; cyclization; selective hydrolysis; synthesis
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