Synthesis Of Nitrogen-containing Heterocyclic Compounds

Supramolecular chemistry is the studies of the interactions between host and guest molecules.Host molecules may selectively bind to guest molecules to form new compounds with new ang unique properties.Over the past two centuries,more than 20 million molecules have been synthesized in the chemical world.These molecules form molecular aggregates through noncovalent bond interactions and self-assemble into high level poly structures with a wide range of structural and functional differences.Supramolecular compounds are complex and ordered macromolecular systems formed by the interaction of host molecules and one or more guest molecules through noncovalent bonds such as hydrogen bonds and coordination bonds.The host molecules are generally electron-rich molecules that can act as electron donors.Many nitrogen-containing compounds are good electron donors.For example,the macrocyclic compounds formed by the condensation of pyrrole and carbonyl compounds retain many the properties of nitrogen atoms to easily form non-covalent bonds with other guest molecules or ions.Porphyrins and calixol are calixpyrroles are macrocyclic compounds.Porphyrins are a large ? system structures with 18 electrons and characteristic aromatic properties and can form complexes with metal ions.Calixpyroles have aromatic-like structures in which our azoles are connected to each other to form cyclic compounds with a cavities that can specifically recognize anions.The work presented in thesis includes the following:1.The synthesis and synthetic optimization of 12 compounds by the allkylation reaction of N-Boc-piperazine,piperazin-2-one with acrylates,acrylonitrile,sultone,and benzyl chloride.Three of these compounds have not been reported in the literature.The hydrolysis of some of these compounds led to the formation of complexing agents with special structures.Tetramethyltetrakis(4-piperidinyl)calipyrrole compounds were prepared,and the Michael reaction of tetramethyltetrakis(4-piperidinyl)calixpyrrole with acrylates and acrylonitrile was optimized with four optimized alkylation reaction conditions for calixol.The alkyl sulfonation reaction of tetramethyl tetrakis(4-piperidinyl)caliperol was also explored.2.Synthesis of five 4-substituted phenylporphyrin compounds from benzaldehyde derivatives and pyrrole,and the optimization for the synthetic methods of these five porphyrin compounds.In addition,a Soxhlet extractor was used for their purification.The purification method for the these porphyrin compounds is simple in operation and high gives high purity products.This method has not been reported in the literature.The hydrolysis of acyl-substituted 4-hydroxyphenylporphyrin compounds has been explored,ane the presence of cyclodextrin was found to facilitate the hydrolysis reaction.The inclusion interaction of ?-cyclodextrin,sulfobutyl-?-cyclodextrin,and hydroxypropyl-?-cyclodextrin with 4-hydroxyphenylporphyrin and their effect on the solubility of porphyrins were also investigated.