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

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

Volume: 5 Issue: 2

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

Affiliation:

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

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.

Cite this article as:

Baharfar Robabeh, nia Hossein Roghayeh and Baghbanian Meysam Seyed, A Novel Approach to the Synthesis of Highly Functionalized Thiophenes Using Isocyanides Catalyzed Reaction of Acetylenic Esters with 3-Mercapto-2-Butanone, Letters in Organic Chemistry 2008; 5 (2) . https://dx.doi.org/10.2174/157017808783744019