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Synthesis 2010(10): 1603-1608  
DOI: 10.1055/s-0029-1219759
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Characterization of New 4-Hydroxy-1,3-thiazoles

Eric Täuschera, Dieter Weiß*a, Rainer Beckert*a, Helmar Görlsb
a Institute of Organic and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstr. 10, 07743 Jena, Germany
Fax: +49(3641)948212; e-Mail: C6bera@uni-jena.de;
b Institute of Inorganic and Analytical Chemistry, Friedrich Schiller University Jena, Lessingstr. 8, 07743 Jena, Germany
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Publication History

Received 12 January 2010
Publication Date:
12 April 2010 (online)

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Abstract

A series of highly substituted 4-hydroxy-1,3-thiazoles was synthesised in two different ways. Whereas their anions display strong fluorescence in the bathochromic part of the visible spectrum, the emission is shifted hypsochromically upon alkylation reactions. This easy switch between the anion and its derivatives makes them suitable for widespread applications. The thiazoles possess prerequisites for the complexation of metals due to the coexistence of aza-heterocycles and of 1,3-diketone substructures. In addition, the hydroxy group allows further functionalisation reactions, as exemplified by the incorporation of an azide or an acetylene into the product, and by the synthesis of a star-shaped derivative.

Key words

heterocycles - condensation - fluorescence - alkynes - azides

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CCDC-755659(1e) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk].