Synthesis 2015; 47(17): 2609-2616
DOI: 10.1055/s-0034-1380655
paper
© Georg Thieme Verlag Stuttgart · New York

Oxidation of Disulfides to Taurine and Sulfanilic Acid Derivatives

Authors

  • Norbert Furtmann

    Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, 53121 Bonn, Germany   eMail: guetschow@uni-bonn.de
  • Erik Gilberg

    Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, 53121 Bonn, Germany   eMail: guetschow@uni-bonn.de
  • Nicola Spütz

    Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, 53121 Bonn, Germany   eMail: guetschow@uni-bonn.de
  • Michael Gütschow*

    Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, 53121 Bonn, Germany   eMail: guetschow@uni-bonn.de
Weitere Informationen

Publikationsverlauf

Received: 04. Februar 2015

Accepted after revision: 30. März 2015

Publikationsdatum:
08. Mai 2015 (online)


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Abstract

Taurine (2-aminoethanesulfonic acid) is a representative substructure in biologically active compounds, but can raise difficulties in direct coupling reactions. In this study, the synthesis of taurine-derived sulfonic acids and analogous aromatic sulfonic acids was accomplished by a performic acid promoted oxidation of corresponding symmetrical disulfide precursors. In some of the products, the taurine or sulfanilic acid nitrogen atom is incorporated in a heterocyclic scaffold or part of a peptide bond in dipeptide mimetics.

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