The Intramolecular Cyclization Construction Of Benzo [6-5-6] Tricyclic And Intermolecular [3+2] Reaction For The Synthesis Of Indane

The thesis mainly consists of the following two parts: PartⅠ: A study of intramolecular Aza-Friedel-Crafts reaction to the construction of Benzo [6-5-6] tricyclic skeletonBenzo [6-5-6] tricyclic skeleton are the core skeleton of some diterpenoids, which are called fluorene compounds. Due to the special photoelectric properties and biological activities of fluorene compounds, it has a very good development prospect in optoelectronic materials and pharmaceutical fields. In this paper, the use of the intramolecular Aza-Friedel-Crafts reaction step to build a cyclopentene ring while generating a carbon and nitrogen bond reaction has not been reported in other reports. By using cheap and readily available acrolein-substituted and amine as raw material, with water is the only by-product, the reaction can be used for efficient construction of carbon ring skeleton and nitrogen heterocyclic skeleton, which has high atomic economy and synthesis efficiency. Intramolecular Aza-Friedel-Crafts reaction of exo-mode has been researched by few people, so the results of this study can enrich the application of the Aza-Friedel-Crafts reaction in organic synthesis, and provide the basis for the study of diversity of active molecules and natural product synthesis. PartⅡ: A study of iron-catalyzed benzyl carbocation and olefin [3+2] cycloaddition reaction to the construction of indane derivativesIndane derivatives is the core skeleton of many natural products, which exist in nature widely. Indane derivatives has many unique characteristics, there are good prospects in pharmaceuticals, pesticides, organic light-emitting materials, photosensitive materials, colorants and so on. This topic using FeCl₃ as catalyst succeeded in activating the benzyl ether bond, in 1,2- dichloroethane solvent by [3+2] cycloaddition obtained indans derivatives. The experimental method has the advantages of simple operation, cheap and readily available raw materials, it has a good substrate pervasive and functional group tolerance, it also showed good stereoselectivity and regioselectivity, broaden study area of the metal catalyzed activation C-O bond, and provided a simple and practical method for building efficient indane derivatives.