A Novel Approach to the Synthesis of Highly Functionalized Thiophenes Using Isocyanides Catalyzed Reaction of Acetylenic Esters with 3-Mercapto-2-Butanone

Author(s): Robabeh Baharfar, Roghayeh Hossein nia, Seyed Meysam Baghbanian.

Journal Name: Letters in Organic Chemistry

Volume 5 , Issue 2 , 2008

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Abstract:

Reaction of 3-mercapto-2-butanone with electron-deficient acetylenic esters in the presence of tert-butyl isocyanide leads to dialkyl 4-hydroxy-4,5-dimethyl-4,5-dihydro-2,3-thiophenedicarboxylates. These alcohols are converted to 2,3-dialkyl-4,5-dimethyl-2,3-tiophenedicarboxylates in boiling dichloromethane in fairly good yields. (E/Z) SFunctionalized vinyl sulfides are produced in this reaction as by- products.

Keywords: t-butyl isocyanide, 3-mercapto-2-butanone, acetylenic esters, vinyl sulfides, thiophenes, SH-acid

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Article Details

VOLUME: 5
ISSUE: 2
Year: 2008
Page: [128 - 132]
Pages: 5
DOI: 10.2174/157017808783744019
Price: $58

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