Organic Reaction Based On The Chiral Imidazolidinone Skeleton And Its Application

In this thesis, the research work focused on the reactions and properties of compounds containing imidazoline skeleton was carried out. There are three parts in this thesis, which were described as follows:Part â…  we have developed a novel synthetic method for the construction of chroman framework containing spirobicyclic N,O-acetal skeleton in moderate to good yields with good to excellent diastereoselectivities(up to > 20:1 dr) via a three-component tandem reaction of phenol, paraformaldehyde, and 5-benzylimidazolidin-4-one promoted by p-nitrobenzoic acid. The features of this protocol include high efficiency(two C-C bonds, one C-O bond, one C-N bond formation in one step), excellent diastereoselectivity, and simple one-pot operation. Preliminary synthetic application shows that the products afforded by our method were anticipated to serve as a precursor for the exploration of visual H+ sensor.Part â…¡ We synthesized a series of imidazolinone compounds containing benzene ring at 2-position, we found that some of them demostrated fluorescence emission when mixed with strong base. We partially confirmed that the fluorescence emission was concerned upon the formation of hydrogen bond interation between N-H group and the substituent in the benzene ring at 2-position.Part â…¢ We synthesized a series of new chiral ligands which containing chiral imidazolidinone skeleton. Preliminatry study showed that some of them were potential chiral ligands in the zinc-catalyzed Friedel-Crafts alkylation of nitroalkenes to indoles.