Synthesis Of Benzo?-lactams Through Non-noble Metal-Catalyzed Ynamide Cyclization

Multiple-substituted Benzo 5-lactams are one of the important motifs with great synthetic value,which widely found in natural products and bioactive compounds.However,among the traditional construction methods,most of them were used the noble metal catalysts,such as rhodium or gold,which greatly limited the industrial applications.Therefore,in this thesis,we developed two kinds of methods to construct the motifs with the catalysis of non-noble metal catalysts.In the first part,we used the pyridine oxide which was the oxygen source of the lactam products to initial the reaction,and then used the electron-riched alkenes or alkynes as the nucleophiles to trap the metal activated ynamides.The non-noble metal catalyzed oxidation of ynamides are able to reduce the cost efficiently,besides,it is differs from the oxidation catalyzed by noble metal,it will not produce the cycloprapanation and over oxidation products.The second part,we used the water to attack the ynamides,and then the enamide intermediates would be trapped by the intramolecular aldehydes,and formed the hydroxyl-substituted quinolinone derivatives with effect.Noteworthy,the reaction yield the syn-selective lactams as the major products,rather than the anti ones.