AlCl₃-Promoted Intramolecular Hydroamidation Of Unactivated Alkenes

Nitrogen-containing organic compounds,which are widely existed in various kinds of pharmaceuticals and natural products,are the basic building blocks in synthetic organic chemistry and medicinal chemistry,and have played important roles in organic synthesis and drug design and synthesis.Therefore,the development of efficient synthesis of nitrogen-containing organic compounds has always been a hot area of research for several decades in the field of organic synthesis.In addition,the formation of C-N bond is one of the most fundamental questions in synthetic organic chemistry,and using unsaturated hydrocarbons as raw materials to synthesize nitrogen-containing organic compounds is one of the most important methods for this purpose due to the easy availability of the starting materials.Among the variety of methods developed,hydroamination,direct addition of N-H bond to unsaturated C-C bond,is one of the most effective strategies for the formation of C-N bonds and the construction of nitrogen-containing bioactive molecules.Consequently,it is of high importance to develop new and efficient methods for the synthesis of nitrogen-containing compounds.In this thesis,AlCl₃-promoted intramolecular hydroamidation of unactivated alkenes was studied.This method has a broad scope of substrates,and has no Thorpe-Ingold restriction,which provides a convenient procedure for the preparation of pyrrolidine and indoline derivatives under mild reaction conditions.Based on the preliminary results,a possible reaction mechanism that involving“six-member ring transition state”and“carbenium ion intermediate”is presented.