Synthesis of 2-(Substituted-silyl)thiophene-3-carboxylates via a Facile [3+2] Cycloaddition Reaction Catalyzed by Potassium tert-Butoxide

Author(s): Yi-Nan Cheng , Wen-Bo Jin , Li-Min Wang , Shu-Jun Sun , Gui-Ying Xie , Xiu-Feng You , Yan-Qin Zhao , Hong-Lian Li .

Journal Name: Letters in Organic Chemistry

Volume 13 , Issue 7 , 2016

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Graphical Abstract:


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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Article Details

Year: 2016
Page: [467 - 473]
Pages: 7
DOI: 10.2174/1570178613666160812102130
Price: $58

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