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Mannich products of kojic acid and N-heterocycles and their Ru(II)-arene complexes: Synthesis, characterization and stability |
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| Authors: | Johanna H Kasser Christian G Hartinger Alexey A Nazarov Vladimir B Arion Bernhard K Keppler |
| Institution: | a Institute of Inorganic Chemistry, University of Vienna, Waehringer Str. 42, A-1090 Vienna, Austria b Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne (EPFL), CH-1015 Lausanne, Switzerland c Research Platform Translational Cancer Therapy Research, University of Vienna, Waehringer Str. 42, A-1090 Vienna, Austria |
| Abstract: | Ru(II)-η6-p-cymene compounds bearing pyrone-derived ligands, which were obtained by Mannich reaction with piperidine and related analogues, have been synthesized. The compounds were characterized by NMR spectroscopy, mass spectrometry, thermogravimetric analysis and in the case of 2-(2,6-dimethyl-morpholin-4-ylmethyl)-3-hydroxy-6-hydroxymethyl-pyran-4-one by X-ray diffraction analysis. The chlorido complexes are prone to aquation in aqueous solution which results in the formation of dimers. Dimer formation can be inhibited by in situ replacement of the chlorido ligand by imidazole yielding compounds which are significantly more stable in water, as demonstrated by 1H NMR spectroscopy. |
| Keywords: | Kojic acid Mannich reaction Ruthenium(II)-arene complexes Stability studies Synthesis |
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