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

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
› Author Affiliations
Further Information

Publication History

Received: 04 February 2015

Accepted after revision: 30 March 2015

Publication Date:
08 May 2015 (online)


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.

Supporting Information

 
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