Features of synthesis and structure of ethyl (2<Emphasis Type="Italic">Z</Emphasis>)-3-hydroxy-(2,3,4,5-tetrafluorophenyl)-propyl-2-enoate |
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Authors: | D N Bazhin E V Shchegol’kov Yu S Kudyakova K V Scherbakov Ya V Burgart V I Saloutin |
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Institution: | 1.Postovskii Institute of Organic Synthesis, Ural Branch,Russian Academy of Sciences,Yekaterinburg,Russia |
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Abstract: | The structure of key intermediates in the synthesis of fluoroquinolone antibiotics: diethyl (2,3,4,5-tetrafluorobenzoyl)malonate
and ethyl (2Z)-3-hydroxy-(2,3,4,5-tetrafluorophenyl)prop-2-enoate was for first time studied using X-ray diffraction (XRD) and 1H, 19F NMR spectroscopy. In solution both the esters were shown to exist as a mixture of enol and ketone tautomeric forms with
predominance of the latter. According to the XRD analysis, ethyl (2Z)-3-hydroxy-(2,3,4,5-tetrafluorophenyl)prop-2-enoate in the solid state exists entirely in the enol form. |
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