Mannich products of kojic acid and N-heterocycles and their Ru(II)–arene complexes: Synthesis, characterization and stability

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.

The Mannich reaction of kojic acid with piperidine and related analogues yields a series of pyrone-derived ligands which were transformed into the respective [RuIICl(cymene)] complexes. Aquation of the complex and related formation of dinuclear Ru species can be inhibited by in situ replacement of the chlorido ligand by imidazole.Figure optionsDownload as PowerPoint slide