Research On The Michael Addition Reaction Of Chalcone Containing Ferrocenyl

Ferrocene is an organometallic compound having a "sandwich structure", which is composed with two cyclopentadienyl (C5H5-) and a bivalent iron (Fe2+) composition. Due to its unique properties such as stability, low toxicity, aromaticity, redox activity and so on, ferrocene and its derivatives have been widely used in the field of functional materials, the medicine and catalysis, etc., such as bridged pyridine compounds and Schiff base containing ferrocene groups can be used as nonlinear optical material and liquid crystal material, platinum metal complex containing ferrocene group is an effective drug for treating cancer, chiral ferrocenyl phosphine ligand show good catalytic activity in the synthesis of chiral asymmetric drugs. Chalcone containing ferrocenyl is a kind of important organic pharmaceutical intermediates, with good biological activity and pharmacological activity, which can be used in anti-tumor, anti-bacterial and anti-virus. Also it can react with active methylene compound by Michael addition reaction, the formation of the macromolecular structure of the compound have the pharmacological activity. Since ferrocene and chalcone have good biological activity and pharmaceutical activity, the Michael addition product with macromolecular structure also have good biological activity.A series of chalcone containing ferrocenyl have been designed and synthesized, then react with a variety of active methylene compounds by Michael addition. Effective addition of active methylene compounds and chalcones containing ferrocenyl, to get drugs intermediates with better antibacterial activity.Firstly, acetyl ferrocene was synthesized in the catalytic of phosphate, with ferrocene as the starting material, acetic anhydride as the acylating agent. The structure was verified by melting point, FT-IR,1H NMR and 13C NMR.Secondly, thirteen ferrocenyl chalcone have been prepared by acetyl ferrocene with benzaldehyde, p-chlorobenzaldehyde, p-fluorobenza ldehyde, p-bromobenzaldehyde, p-tolualdehyde, p-anisaldehyde, cuminaldehyde, cinnama ldehyde,2-thienyl formaldehyde,3-thienyl formaldehyde, pyridine-2-carbaldeh yde, m-nitrobenzaldehyde, p-nitrobenzaldehyde by solid-phase method, respectively, with solid base as catalyst. The reaction time, feed ratio and catalysts have been discussed by single factor method, with the reaction of acetyl ferrocene and benzaldehyde as an example, the optimal reaction conditions were: NaOH and anhydrous K2CO3 as catalyst, the molar ratio of ferrocene and aromatic aldehydes is 1:1.2, the reaction time is 5-10min.Finally, ferrocenyl chalcone reacted with thirteen kinds of active methylene compound, diethyl malonate, cyanoethyl acetate, ethyl acetoacetate, nitrome thane, acetylacetone, malononitrile, cyclohexanone, cyclopentanone, barbituric acid, thiobarbituric acid, acetonitrile acetone, respectively. And the optimal reaction conditions were optimized by corresponding surface methodology, with the reaction of ferrocenyl chalcone and diethyl malonate as an example. The optimal reaction conditions are:Anhydrous K2CO3 as catalyst, The molar ratio of ferrocenyl chalcone and active methylene compound is 1:1.23, the reaction time is 0.53h, the yield can be up to 90.70%.