硅烷化
环加成
化学
噻吩
催化作用
钾
有机化学
药物化学
作者
Yuyu Cheng,Wenbo Jin,Limin Wang,Shujun Sun,Guiying Xie,Xiu-Feng You,Yan‐Qin Zhao,Honglian Li
出处
期刊:Letters in Organic Chemistry
[Bentham Science]
日期:2016-10-25
卷期号:13 (7): 467-473
被引量:2
标识
DOI:10.2174/1570178613666160812102130
摘要
Background: Substituted-silyl thiophene carboxylates are important intermediates for the synthesis of substituted-silyl thiophene carboxamides which have been found to show high biological activities. Methods: Using α-mercapto ketones and 3-(substituted-silyl)propiolates as raw materials, 2-(substituted-silyl)thiophene-3-carboxylates could be synthesized smoothly via cycloaddition reaction catalyzed by potassium tert-butoxide. Results: A small library of target compounds was prepared under optimized reaction conditions in moderate to good yields. The reaction mechanism has been proposed. Conclusion: Potassium tert-butoxide is an environmentally friendly and efficient catalyst for the cycloaddition reaction of α -mercapto ketones and 3-(substituted-silyl)propiolates. This methodology provides ready access to 2-(substituted-silyl)thiophene-3-carboxylic acids which can be serve as the raw materials of 2-(substituted-silyl)thiophene-3-carboxamide and other pharmaceutically intriguing compounds. Keywords: 2-(Substituted-silyl)thiophene-3-carboxylate, cycloaddition, α -mercapto ketone, 3-(substituted-silyl)propiolate, catalysis.
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