Studies On Application Of 2-(p-tosyl) Phenol Compounds In Organic Synthesis

ortho-Quinone methide(o-QMs)have been attracted much attention by organic chemists due to their special structure and activity,and have been widely used in the synthesis of various complex polycyclic compounds as well as natural products.In this dissertation,we focus on the nucleophilic reaction of o-QMs intermediate with organic zinc reagents.The dissertation is mainly divided into three chapters:The application of o-QMs in organic synthesis was reviewed in the first chapter.In the second chapter,the conjugated alkynylation of 2-(p-toluenesulfonyl)phenol compounds and its application in the synthesis of 2,3-disubstituted benzofurans were studied.We obtained a good yield of alkynyl phenolic compounds through the reaction of 2-(p-toluenesulfonyl)phenol in-situ generating o-QMs intermediates with zinc reagents.On this basis,we developed a one-pot synthesis of 2,3-disubstituted benzofuran compounds.In the third chapter,the synthesis of functionalized triarylmethane compounds using 2-(p-toluenesulfonyl)phenol and aryl zinc reagents was studied.The differently substituted 2-(p-toluenesulfonyl)phenol compounds were reacted with different zinc reagents.Series of functionalized triaryl compounds were synthesed by [1,4] addition of o-QMs intermediates.This reaction can be used to synthesize a class of antituberculosis agents and active antiviral derivatives.