A New Procedure for Synthesizing 4,5-Dimethyl-2-(trimethylsilyl)-thiophene-3-carboxamide Derivatives

doi:10.6023/cjoc201406006

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (11): 2376-2381.DOI: 10.6023/cjoc201406006 Previous Articles Next Articles

Notes

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

靳文波^a, 谢桂英^a,b, 孙淑君^a,b, 赵艳芹^a, 程绎南^a,b, 孙炳剑^a,b, 李洪连^a,b

a 河南农业大学植保学院郑州 450002;
b 新型农药创制与应用河南省重点实验室郑州 450002

收稿日期:2014-06-06 修回日期:2014-06-20 发布日期:2014-07-03
通讯作者: 程绎南,chyn212@aliyun.com;李洪连,honglianli@sina.com E-mail:chyn212@aliyun.com;honglianli@sina.com
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

Jin Wenbo^a, Xie Guiying^a,b, Sun Shujun^a,b, Zhao Yanqin^a, Cheng Yi-nan^a,b, Sun Bingjian^a,b, Li Honglian^a,b

a Plant Protection College, Henan Agricultural University, Zhengzhou 450002;
b Henan Provincial Key Laboratory of the Discovery and Application of Novel Pesticide, Zhengzhou 450002

Received:2014-06-06 Revised:2014-06-20 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).

1. A New Procedure for Synthesizing 4,5-Dimethyl-2-(trimethylsilyl)-thiophene-3-carboxamide Derivatives.PDF(2444KB)

Abstract

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

Cite this article

Jin Wenbo, Xie Guiying, Sun Shujun, Zhao Yanqin, Cheng Yi-nan, Sun Bingjian, Li Honglian. A New Procedure for Synthesizing 4,5-Dimethyl-2-(trimethylsilyl)-thiophene-3-carboxamide Derivatives[J]. Chin. J. Org. Chem., 2014, 34(11): 2376-2381.

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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

A New Procedure for Synthesizing 4,5-Dimethyl-2-(trimethylsilyl)-thiophene-3-carboxamide Derivatives

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