Ferrocenyl pyrazolines: Preparation, structure, redox properties and DFT study on regioselective ring-closure
作者： Virág Zsoldos-Mády , Oliver Ozohanics , Antal Csámpai , Veronika Kudar , Dávid Frigyes
DOI: 10.1016/J.JORGANCHEM.2009.09.007
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摘要: Abstract Cyclocondensation of 1-phenyl-3-ferrocenyl-2-propen-1-one (1) with RNHNH2 hydrazines and the substituent-dependent product distribution were investigated. With methylhydrazine, formation two regioisomeric pairs pyrazolines pyrazoles was observed. The ratio products varied solvent temperature. Transformation 5-ferrocenyl-N-substituted into systematically studied DDQ found to be most suitable reagent. Mechanism cyclization reactions taking place under kinetic- thermodynamic controls supported DFT calculations. energy-dependence transformation pyrazoline pyrazole investigated also by EI MS. Structure determination new compounds performed IR, MS NMR methods including 2D-HMQC, 2D-HMBC, DEPT DIFFNOE measurements. For structures proved X-ray diffraction.
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