Synthesis And Catalytic Properties Researches Of Isoxazol (in) E Derivatives Containing Ferrocene

Amongst five-membered heterocycles, isoxazol(in)es represent a class of compounds of great importance in organic synthesis, the discovery and development of drugs, catalytic reactions and the area of electrochemistry because of their particular chemical structures and intrinsic biological activities. So isoxazol(in)es become one of important subjects for organic synthesis and drug chemistry. On the other hand, since the discovery of ferrocene, it and its derivatives have been applied in many areas due to their aromaticity, redox activity, stability and low toxicity. It has been a research focus that incorporating ferrocene into another molecules in order to get some new compounds which could possess some unique characters. As continuation of our previous studies, we have mainly synthesized nine novel-structure isoxazol(in)es containing ferrocene via the 1,3-dipolar cycloaddition reaction, and then focused on the study of catalytic properties of these new isoxazol(in)es.To be specific, nine novel isoxazol(in)es containing ferrocene were firstly obtained via 1,3-dipolar cycloaddition by treating ethynylferrocene, vinylferrocene andα,β-unsaturated ferrocene derivatives with nitrile oxides which derived from substituted benzaldehyde, pyridine-2-formaldehyde and 2,6-pyridinedicarboxaldehyde. These new compounds were characterized by 1HNMR, 13CNMR, FT-IR, mass spectroscopy and elemental analyse. And the structures of 2-(5-ferrocenylisoxazoline-3-yl)p yridine 7and 1,3-bis(5-ferrocenylisoxazoline-3-yl)benzene 8 were further determined by X- r aydiffraction. T he catalytic activity of 1,3-bis(5-ferrocenyli soxazoline-3-yl)benzene 8 as a ligand used in Heck and Sonogashiracoupling reaction was then tested in the present of palladium(II) acetate. The resultshowed 1,3-bis(5-ferrocenylisoxazoline-3-yl)benzene 8 was an effic ient, stable ligand of palladium, and its applications in other reactions were carrying out in our group.