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Synthesis 2012; 44(14): 2225-2230
DOI: 10.1055/s-0031-1289773
DOI: 10.1055/s-0031-1289773
paper
Synthesis of Homotaurine and 1-Substituted Homotaurines from α,β-Unsaturated Nitriles
Further Information
Publication History
Received: 03 April 2012
Accepted after revision: 02 May 2012
Publication Date:
13 June 2012 (online)
Abstract
Homotaurine and a series of 1-substituted homotaurines were readily synthesized in satisfactory to good yields via the Michael addition of thioacetic acid to aliphatic and aromatic α,β-unsaturated nitriles followed by lithium aluminum hydride mediated reduction and performic acid oxidation. The synthesis of 1,1-disubstituted homotaurines was attempted with β,β-disubstituted acrylonitriles as starting materials but failed due to steric hindrance. The current process is an efficient method for the synthesis of 1-substituted homotaurines.
Key words
acrylonitrile - amino thiols - Michael addition - nucleophile - reduction - oxidation - thioacetic acidSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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