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DOI: 10.1055/s-0029-1219759
Synthesis and Characterization of New 4-Hydroxy-1,3-thiazoles
Publikationsverlauf
Publikationsdatum:
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
- 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.
References
Menzel R., Täuscher E., Weiß D., Beckert R., Görls H.; Z. Anorg. Allg. Chem.; accepted
10Nonius B. V.; COLLECT, Data Collection Software; Netherlands, 1998.
14CCDC-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].