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

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

References

• 1 Liebscher J. Houben-Weyl Methoden der Organischen Chemie   4th ed., Vol. E8b:  Georg Thieme Verlag; Stuttgart: 1994.  p.1 ; and references therein
• 2 Kedersky FAJ. Holms JH. Moore JL. Bell RL. Dyer RD. Carter GW. Brooks DW. J. Med. Chem.  1991,  34:  2158 
• 3 Rzasa RM. Kaller MR. Lia G. Magal E. Nguyen TT. Osslund TD. Powers D. Satora VS. Viswanadhan VN. Wang H.-L. Xiong X. Zhong W. Norman HM. Bioorg. Med. Chem.  2007,  15:  6574 
• 5a Stippich K. Weiß D. Güther A. Görls H. Beckert R. J. Sulfur Chem.  2009,  30:  109 
• 5b Grummt U.-W. Weiss D. Birckner E. Beckert R. J. Phys. Chem. A  2007,  111:  1104 
• 6 Crane LJ. Anastassiadou M. Stigliani J.-L. Baziard-Mouysset G. Payard M. Tetrahedron  2004,  60:  5325 
• 7 Becker HGO. Berger W. Domschke G. Fanghänel E. Faust J. Fischer M. Gentz F. Gewald K. Gluch R. Mayer R. Müller K. Pavel D. Schmidt H. Schollberg K. Schwetlick K. Seiler E. Zeppenfeld G. Beckert R. Habicher WD. Knölker H.-J. Metz P. Organikum   23rd ed.:  Wiley-VCH; Weinheim: 2009.  p.208 
• 8a Goerdeler J. Schimpf R. Chem. Ber.  1973,  1496 
• 8b Barrett GC. Tetrahedron  1980,  36:  2023 
• 8c Jensen KA. Crossland I. Acta Chem. Scand.  1963,  17:  44 
• 9 Wagner G. Voigt B. Dänicke D. Pharmazie  1976,  31:  528 
• 11 Otwinowski W. Minor W. Processing of X-ray Diffraction Data Collected in Oscillation Mode, Macromolecular Crystallography, In Methods in Enzymology   Vol. 276, Part A:  Carter CW. Sweet RM. Academic Press; New York: 1997.  p.307 
• 12 Sheldrick GM. Acta Crystallogr., Sect. A  1990,  46:  467 
• 13 Sheldrick GM. SHELXL-97   University of Göttingen; Germany: 1997. 

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Menzel R., Täuscher E., Weiß D., Beckert R., Görls H.; Z. Anorg. Allg. Chem.; accepted

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Nonius B. V.; COLLECT, Data Collection Software; Netherlands, 1998.

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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: [phone]; or [e-mail]].