Tandem Reactions Of ?,?-unsaturated Ketones For The Construction Of Fused Nitrogen-containing Heterocycles

Nitrogen-containing fused heterocyclic compounds are widely present in natural products and drugs.Due to the presence of nitrogen atom,such compounds have a wide range of applications in organic functional materials and drug molecules.Therefore,the development of new,simple and efficient methods to construct this kind of compounds has attracted considerable interest from organic chemists.In this thesis,three kinds of ?,?-unsaturated ketones were employed as substrates to construct a variety of fused heterocyclic compounds.9H-Pyrrolo[1,2-a]indole and its analogs are important structural units of many natural products and drugs,which exhibit interesting biological activities.In the second chapter of this paper,the first copper-catalyzed Friedel-Crafts alkylation/cyclization/isomerization sequence of 3-aroylcoumarins and 3-methylindole was achieved,delivering a wide range of functionalized coumarin fused 9H-pyrrolo[1,2-a]indoles,with a 6-6-5-5-6 pentacyclic core in 34-99% yields..In the third chapter,the first p-TSA-catalyzed highly diastereoselective Michael addition/cyclization of ortho-hydroxychalcones and 3-carboxylate-substituted isoindolinones was developed to access a wide range of chroman-bridged polycyclic isoindolinones.The salient features include easily available materials,mild reaction conditions,broad substrate scope,excellent diastereoselectivity,and simple purification procedures.In the fourth chapter,the 1,3-dipolar cycloaddition/oxidation sequence of methyleneindolinones and quinolinium salts was realized to afford a series of quinoline fused pyrroles in up to 95% yield.This reaction features mild conditions,easily accessible substrates and simple operation.