Palladium - Catalyzed Aromatization Of 2 - Pyridylaldoxime Ether: Stereoselective Synthesis Of (E) - 2 - Pyridyl Aryl Ketone Oxime Ether

Ketoxime ethers are widely present in pharmaceuticals and agrochemicals. The E or Z regioisomer of the ketoxime ethers usually displays different physical property and biological activity. Therefore, development of method to produce ketoxime ethers stereoselectively is very important. Traditional methods to prepare ketoxime ethers lack stereocontrol, require multi steps and suffer low reaction efficiency. In this thesis, we describe an efficient method to prepare (E)-(di)azinylaryl ketoxime ethers through direct arylation of (di)azinyl aldoxime ethers by aryl iodides under PdCl2(PPh3)2/AgOAc catalysis. We have completed the formal synthesis of the potent Merck melanin-concentrating hormone1receptor antagonist using our method.The thesis consists of three chapters:The first chapter contains the following parts:(1) The importance of C-H activation;(2) The applications of the ketoxime ethers in the organic synthesis;(3) The progress of imine N=C-H activation and arylation under metal catalysis;(4) The applications of ketoxime ethers in the medicinal and agricultural chemistry;(5) Conventional methods to prepare Z or E regioisomer of ketoxime ethers.The second chapter contains the following parts:(1) The optimization of the reaction conditions;(2) The substrate scope of reaction;(3) The synthetic application of the method;(4) The experimental procedure, data and spectra of the products.The third chapter is the summary of the thesis.