Thesis/Dissertation Guide For Postgraduates Of Northwest University

The quinolone scaffold is present in many natural products and is regarded as an important block for medicinal chemistry, with simple and flexible synthetic routes that allow the production of large chemical libraries of potential bioactive molecules. Consequently, numerous synthetic strategies have been developed to gain access to different varieties of this scaffold.2-Aryl-2,3-dihydro-4-quinolones represent a new class of antimitotic antitumor agents. Since their two enantiomers were found to display distinctly different activities, a highly enantioselective synthesis of these compounds is desirable.To date, there are only several reports of the catalytic enantioenriched synthesis of 2-aryl-2,3-dihydro-4-quinolones, mainly employing two strategies:one is the asymmetric intermolecular 1,4-addition of organometallic reagents to 4-quinolones; the other is the asymmetric intramolecular aza-Michael addition.For chiral compounds, a single configuration plays an important role, especially in recent years, in the fields of pesticide, medicine, and materials chemistry plays an important role. In numerous enantioselective synthesis method, organocatalysts is one of the most effective method to get the optical purity compound by utilizing chiral catalysts and auxiliaries. In a variety of organic reactions strategy, the one-pot method is a powerful method, in which a variety of starting materials builds more chemical bond and forms a new compound by one step. The strategycombiningorganocatalyst with one-pot strategy must become an extremely effective method for asymmetric synthesis.In summary, we have developed a highly efficient organocatalytic one-pot synthesis of (R)-2-aryl-2,3-dihydro-4-quinolones from o-aminoacetophenones and aryl aldehydes. The products were obtained in good yields with up to 99% ee. Compared to previous approaches, the approach was characterized by metal free, solvent free and protecting group free. Preliminary mechanism study showed that the protocol probably underwent an asymmetric Mannich process. Due to easy operation and high efficiency, this method would be prospective in the synthesis of bioactive 2-aryl-2,3-dihydro-4-quinolones, thereby facilitating biological and medicinal chemistry studies of such compounds.