Preparation Of Silicon-containing Indoline Derivatives By Free Radical Cascade Reaction

Indoline,also known as benzopyrrolidine or 2,3-indoline,is an aromatic heterocyclic compound,which is widely found in natural products and pharmaceutical molecules.It is also used as a characteristic fragment in new pharmaceuticals,and has a wide range of applications.Organosilane plays an extremely important role in many fields such as agricultural chemistry,medicinal chemistry,and material chemistry.At the same time,it is also an important synthesizer in many organic reactions,and can carry out a series of transformation applications,such as Heck reaction,Murai reaction,oxidation reaction and so on.Therefore,the introduction of organosilicon into the indoline framework will greatly expand the scope of indoline derivatives,and is of great significance to the development of indoline compounds.In view of the scarcity of existing methods to synthesize silicon-containing indoline,this thesis introduces a synthetic strategy of silicon-containing indoline by intramolecular cyclization which initiated by free radicals.The first chapter briefly describes the development of tris(trimethylsilyl)silyl radicals and the reaction types,then we briefly summarizes three main synthetic methods of indoline including metal-catalyzed reaction,organic-catalyzed reaction,and free radical cyclization reaction.The second chapter briefly explains the importance of introducing organosilicon into indoline compounds and the basis of reaction design.It was discovered that the silicon free radical initiated by azobisisobutyronitrile can obtain silicon-containing indoline through free radical cyclization and 1,5-hydrogen transfer pathway.This reaction greatly expands the range of indoline derivatives,and has potential applications in pharmaceutical synthesis.The third chapter describes the preparation of starting materials and indoline derivatives,the transformation of the silicon-containing indolines,and the data characterization of the unknown compounds.