Synthesis Of Piperine Derivatives And Homoallylamines Via Coupling Reaction Of Nitrobenzene

Piperine derivatives and homoallylamine compounds containing dienamide structure have high application value in the field of medicine and chemical industry because of their good biological activity and medicinal value,and have been regarded as important in organic synthesis.However,the traditional methods for synthesizing piperine derivatives and homoallylamine compounds generally have some defects,such as: harsh reaction conditions,limited substrate range,cumbersome operation,etc.Compared with amine compounds,nitrobenzene is an attractive nitrogen source due to its low cost and wide availability.The main research direction of our research group in recent years is the functionalization reaction of nitrobenzene.This thesis mainly introduces palladium catalyzed stereo-convergent aminocarbonylation of 1,3-dienes with nitrobenzene:synthesis of(E,E)-dienamides,molybdenum mediated hydroamination of vinylcyclopropanes with nitrobenzene: synthesis of homoallylamines.The first part introduces the palladium-catalyzed carbonylation of nitrobenzene with conjugated dienes to form dienamides.We use nitrobenzene and conjugated dienes as reaction raw materials,and realize the synthesis of a series of dienamides through carbonylation under the joint action of palladium catalyst and ligand.It is worth noting that the reaction proceeds in a highly stereoconvergent manner,in which the conjugated diene derivatives used as raw materials are mostly mixtures of E/Z isomers.The second part introduces the molybdenum-catalyzed coupling reaction of nitrobenzene and cyclopropylvinylbenzene to synthesize homoallylamine compounds.We used nitrobenzene and cyclopropylvinylbenzene as reaction raw materials to realize the synthesis of a series of homoallylamine compounds through coupling reaction under the action of molybdenum catalyst.The reaction substrate has wide application range,good yield and simple operation.