Research On Green Chemical Synthesis And Application Expansion Of 2,3-Naphthalimide,Aryldihydronaphthalene And Succinimide Skeletons

2,3-Naphthalimide,aryldihydronaphthalene and succinimide skeletons are three very important skeleton types.2,3-Naphthalimide can be used as a fluorescent labeling material and environmentally sensitive fluorescent probes for imaging analysis of drug molecules and pharmacologically active molecules in vivo,etc.;Aryldihydronaphthalene and succinimide skeletons can be found in some pharmacologically active molecules and natural products or drug structures.Therefore,the construction of these three types of frameworks is of great significance to the fields of biochemistry and medicinal chemistry.However,the existing methods for synthesizing these types of compounds are suffered from cumbersome routes,low yields and poor compatibility of functional groups,which limits its' applications to a certain extent.Therefore,it is still very important to develop a new method with high efficiency and wide substrate scope.In recent years,green chemistry has been favored by the majority of chemical synthetic researchers,not only because it can reduce the cost of the reaction,but more importantly,it can reduce the use of transition metal catalysts in the synthetic process,thereby reducing environmental pollution.Three synthetic approaches for the construction of 2,3-naphthalimide,aryldihydronaphthalene and succinimide compounds were proposed,and related applications of these methods were conducted.The research provides green and practical synthetic routes for the construction of these types of compounds with potential pharmacological activities and medicinal values.The thesis is based on the certain activation effect of the imide fragment to the alkynyl group and a suitable substrate configuration,which can promote the synthesis of 2,3-Naphthalimide via an intramolecular didehydro-Diels-Alder(DDDA)reaction of styrene-yne-imide compounds.This method avoids the utilization of expensive or toxic metal catalysts and ligands,and features in high atom economy,mild reaction conditions and good compatibility with different functional groups,which provides a simple and mild synthetic pathway for the fluorescence 2,3-naphthalimides.Based on the research on the intramolecular DDDA reaction under mild reaction conditions,which are promoted by the above-mentioned propiolimide fragment,together with the research background that the aryldihydronaphthalene skeleton is widely existed in natural products and biologically active substances.In this paper,the investigation on the dehydro-Diels-Alder reaction from the styrene-alkynes,which offers an alternative and green synthesis process for the construction of the important aryldihydronaphthalene skeletons.Based on the study of the intramolecular DDDA reaction of styrene-ynes promoted by the propiolimide fragment,together with the important application of the succinimide skeletons in drugs and pharmacologically active substances.In this paper,we realized the synthesis of succinimide skeletons via an intramolecular Alder-ene reaction through the propiolimide compounds containing 1,6-enynes moieties under relatively mild and metal-free conditions;this method can fulfill the structural modification of complex natural products and pharmacologically active molecules in the late stages,avoiding the problem of metal residues in the chemical synthesis process,which not only provides a green and economical synthetic apprach for the construction of succinimide compounds,and also laid the foundation for the cyclization of other enyne type substrates promoted by the propiolimide moiety.