Synthesis of Homotaurine and 1-Substituted Homotaurines from α,β-Unsaturated Nitriles

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 acid

• References

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