Palladium-catalyzed Cyclization Of Allenamines To Construct Polycyclic Systems

Allenamines have become important precursors in organic synthesis,and the reaction research of allenamines is of great significance for the design and synthesis of biologically active molecules and natural products.Due to the unique reactivity and high selectivity of allenamine,it is often used as a series of heterocyclic compounds such as indole,quinoline,pyrrole,pyridine and a series of enamine and allylamine derivatives.At present,the commonly used strategy to construct functionalized indole quinoline derivatives is to use functionalized indole derivatives or complex aromatic compounds as multi-functional raw materials to synthesize these indole quinoline derivatives,but generally requires lengthy multi-step synthesis.According to the previous reported synthesis methods,the difficulty in obtaining these target molecules mainly lies in how to construct the skeleton of pyrrolidone piperidine.In this thesis,we focus on the transition metal palladium catalysis,and study the construction of indolequinoline polycyclic system by using allene amine compounds and o-iodoaniline derivatives.The optimal reaction conditions,substrate universality and other aspects of the reaction were investigated in depth,and a possible reaction mechanism was proposed,thus providing new ideas and methods for the construction of indolequinoline derivatives.The contents are as follows:Based on the characteristics of the cyclization reaction of allene amine,this study was designed to apply diene amine to the construction of a polycyclic reaction,and successfully realized the palladium catalyzed reaction of building quinoline indole skeleton from diene amine compounds.Based on allene amine derivatives and o-iodobenzamine derivatives,a series of polycyclic compounds containing indole quinoline skeleton were constructed through two consecutive Heck reactions in one pot,and a series of indole quinoline derivatives were efficiently obtained.The reaction system is characterized by mild reaction conditions,good substrate tolerance,and simple raw materials.