Synthesis and characterization of new crown-type compounds with 4-pyrone Units |
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| Authors: | Werner Löwe Stefanie Brätter Christoph Dietrich Manuela Weber Peter Luger |
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| Affiliation: | 1. Institut für Pharmazie I, Freie Universität Berlin, Königin-Luise-Str. 2+4, D-14195 Berlin, Germany;2. Institut für Kristallographie, Freie Universität Berlin, Takustr. 6, D-14195 Berlin, Germany |
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| Abstract: | We report here the syntheses and characterization of new crown-type compounds 8 and 9 incorporated with one and two 4-pyrone units. The reaction of compound 3 with 1,5-bis(2-hydroxyphenoxy)-3-oxapentane or catechol gave the desired molecules 8 and 9 in 65% and 25% yields, respectively. Compound 3 resulted from 1 by Wohl-Ziegler bromination in small amounts and could be separated from five bromination by-products by column chromatography. For example, 8 binds K+ and a pyrylium salt 11 (single crystal X-ray structure analysis) can also be prepared starting from 3 by treatment of the latter with perchloric acid in the presence of acetonitrile. |
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