The Study Of Acid Catalyst-control Selective Synthesis And Biological Activity Of Cyclohex-2-enone Derivatives

Acid-catalyzed Aldol condensation reactions of aldehydes with ketones are important reactions of C-C bond formation in organic synthesis,they play important roles in the research of organic synthetic chemistry.The reactions can be carried out in organic solvents,non-organic solvents,and even solvent-free.But microwave-assisted catalyzation techniques can simplify experimental operations,improve yields and increase reaction rates.The techniques used in organic synthesis are conducive to save manpowers,materials and financial resources.Therefore,the use of microwave-assisted catalyzation techniques for solvent-free organic reactions is concerned in recent years and potential for development.The main work presented in this dissertation is about the study of Acid catalyst-control selective synthesis and biological activity of cyclohex-2—enone derivatives.The contents are listed as the following:1,Aldol condensation reactions of a series of aromatic ketones,diethyl malonate with aromatic aldehydes were carried out readily in excellent yields.And the influence of the power of the microwave iradiation was investigated.The current method offers several advantages including high yields,good selectivity,the use of BiCl₃ as an inexpensive catalyst,solvent-free,simple experimental procedure.And this method of microwave-assisted Aldol condensation of aromatic ketones,diethyl malonate with aromatic aldehydes appears to be unprecedented.2,A rapid and eficient method for Aldol condensation of 5-substituted 3-methyl cyclohex-2-enone derivatives with aromatic aldehydes under completely solvent-free conditions has been developed in a good selectivity,which was achieved by microwave iradiation in the presence of Lewis acid such as BiCl₃.The effects of other Lewis acid catalysts on the reaction have also been investigated.In this method, the process is enviromentally benign,the experimental procedure is very simple,and the selectivity is good.Furthermore,this method of microwave-assisted condensation of 5-substituted 3-methyl cyclohex-2-enone derivatives with aromatic aldehydes appears to be unprecedented.We have optimized the condensation conditions and detected the application field.We get 5 condensation products of cyclohexenone compounds with aromatic aldehydes,but with the effects of the catalyst,the reaction substrates,reaction conditions,the reaction has not been fully carried out.3,On the base of microwave-assisted Lewis acid-catalyzed reactions,we use 5-substituted 3-methyl cyclohex-2-enone derivatives as substrates for microwave-assisted protonic acid such as p-toluenesulfonic acid catalyzed condensation reaction,and get 16 condensation products of cyclohexenone derivatives and aromatic aldehydes with high yields and good selectivity.The Aldol condensation products and the method of microwave-assisted condensation of 5-substituted 3-methyl cyclohex-2-enone derivatives with aromatic aldehydes catalyzed by p-toluenesulfonic acid appear to be unprecedented.We have optimized the condensation conditions and detected the application field.4,As a result,compound 8c showed protective activity of cardiovascular endothelial cells.It laid a foundation for the research of the biological effect of these compounds.