Study On The Diversity Synthesis Of Isoindolinones

Isoindolinones is a kind of common privileged skeleton,which widely present in natural products and drug molecules.Therefore,the development of methods for the synthesis of these molecules have captured organic synthesis workers' wide attention.This dissertation focuses on the green synthetic methodologies of 3-hydroxyisoindolinones and metal-free selective and diverse synthesis of two distinct sets of isoindolinones.Chapter 1 presents the green synthesis methods of 3-hydroxyisoindolinone.Using o-alkynylbenzoic acids and primary amines as substrates,and water as solvent,3-hydroxyisoindolinones were rapidly and efficiently constructed without catalyst and additive.This protocol features green synthesis,good to high yields,high bond-forming efficiency,excellent selectivity,extraordinarily broad substrate scope and high atom economy,thus providing aconvenient and highly efficient access to 3-hydroxyisoindolinones.In addition,this method can be further developed into a two-step one-pot tandem reaction for the rapid construction of isoindolinone fused heterocyclic compounds.Chapter 2 presents metal-free selective and diverse synthesis of two distinct sets of isoindolinones.This method realized selective and diverse synthesis of 3-methyleneisoindolinones,5,6-dihydroisoindolo[1,2-a]isoquinolin-8(12bH)-ones in a reaction-condition-controlled manner from 2-alkynylbenzoic acids and amines.This method exhibits valuable advantageous features such as available starting materials,broad substrate scope,excellent selectivity,good to high yields,good functional group tolerance,simple operation,high bond-forming efficiency and step economy,thus providing a convenient and efficient access to a variety of heterocyclic compounds incorporating the isoindolinone motif.