Studies On The Synthesis Of Aza-macrolides Via Iridium Catalysis And Their Fluorescene Properties

Macrolides are important branches of macrocyclic compounds,and are widely present in natural products and bioactive molecules.In the light of their unique structurals,macrolides could be applied as fluorescent sensing moleculars.Therefore,it is important to develop convenient and efficient protocols for the macrolide constructions.However,the preparing methods of such compounds are currently limited to transition-metal-catalyzed intramolecular cyclizations,which usually require multiple steps to access to the starting materials.Meanwhile,the structure of the macrocyclic products lacks diversity,which is not conducive to derivatization.The rapid construction of functional organic molecules from readily available starting materials has been a research hotspot in syntheses.Among them,the tandem cyclization protocols usually employ simple and readily available substrates to conveniently and efficiently achieve a series of transformations by means of avoiding tedious synthetic steps as well as reducing chemical wastes,which has become an important tool to access to various important heterocyclic skeletons.In this thesis,we have develope the first iridium-catalyzed intermolecular decarboxylative reaction of vinylethylene carbonates(VECs)and isatoic anhydrides,which successfully deliver to a series of 14-membered aza-benzomacrolides.The cyclization features cheap and easily obtained starting materials,mild reaction conditions,simple operation,and CO2 as the side-product.Preliminary mechanism investigations shows that this conversion is achieved through the allylic amination/ macrolactone tandem process.Furthermore,experiments such as fluorescence emission,ultraviolet absorption as well fluorescence quantum determination indicate that the aza-macrolides behave unique fluorescent properties,which are expected to be applied to light-emitting materials and biosensors.