Direct Construction Of 2-Acetylquinazolin-4-ones Via Self-sequential Stratege Of Domino Reactions

Based on the requiment of environmentally friend,efficient and atom-economic synthetic methods in modern society,domino reaction strategy has been developed to perfom some related reactions simultaneously in a single reaction vessel and directly gain the products.So far,there are many reviews about domino reactions,it's an important and interesting topic to help people for their design and construction of complex molecules and some nature products.On the basis of this concept,in this dissertation,we have investigated direct construction of 2-acetylquinazolin-4-ones via self-sequential stratege of domino reaction.We obtained the two desired compounds for the highly selective sequential addition of the substrates and disclosed the possible mechanism by controlled experiments.The main content is as follows:In chapter 1,we highlighted the the application of domino reactions in organic synthesis,the synthetic methods of quinazolinones,the found and total synthesis of Luotonin F.Subsequently,we put forward our research topics based on the idea of self-sequential stratege of domino reactions.In chapter 2,inspired by the cognition of the importance of domino reactions and quinazolinones,through a rational logical design,we proposed an efficient one-pot,one-step synthetic protocol for the synthesis of 2-acetylquinazolin-4-ones,which contained a natural product.In this reaction,simple and readily available methyl ketones and o-aminobenzamides were used as substrates to afford 2-acetylquinazolin-4-ones.This method offered a powerful evidence for the total synthesis of nature products.More importantly,based on the controlled experiments,the reaction mechanism was supposed to be multifundamental reaction(iodination,Kornblum oxidation,and annulation).All the compounds of 2-acetylquinazolin-4-ones are characterized by 1H NMR,13C NMR,IR and HRMS.In additional,one compound is further confirmed by X-ray single crystal diffraction.In chapter 3,as aryl iodides are important intermediates in organic chemistry,we hypothesized that a highly selectivity synthesis of 2-benzoyl-6-iodoquinazolin-4-ones have been developed.Meanwhile,based on the controlled experiments,the reaction mechanism was supposed to be multifundamental reaction(iodination,Komblum oxidation,and annulation).