Palladium Catalyzed Selective Coupling Reaction Of Synthetic Quinolone Compounds And Certain The Decarboxylation Coupling Reaction

This thesis includes three parts as the following:1.The palladium-catalyzed regioselective cross-coupling reactions of 3-bromo-4-tosyloxy-quinolin-2(1H)-one with arylboronic acids via diversity-oriented synthesis provide a simple,general,efficient,and practical synthesis of 3, 4-disubstituted quinolin-2(1H)-ones.Subsequently,the KDR kinase inhibitor via palladium-catalyzed regioselective cross-coupling reaction and Cul-mediated cyclization process was synthesized in good yields.Meanwhile,the biologically active 3-amino-4-arylquinolin-2(1H)-ones and 3-alkenyl-4-arylquinolin-2(1H)-ones via palladium-catalyzed site-selective Suzuki-Miyaura/Buchwald-Hartwig amination and Suzuki-Miyaura/Heck coupling reactions were generated starting from 4-hydroxyquinolin-2(1H)-one.2.The combination of palladium chloride with BINAP shows high efficiency in the decarboxylative cross-coupling reactions of arenecarboxylic acids with aryl iodides or aryl bromide.The reactions proceed smoothly to generate the corresponding biaryl compounds in good to excellent yields.Subsequently,a highly effective decarboxylative cross-coupling reaction of cinnamic acid with aryl iodide was realized catalyzed by the combination of palladium chloride and CyJohnPhos in the presence of Ag₂CO₃ as additive.The desired carbon-carbon bond formation proceeds efficiently with good functional-group tolerance.3.Iron(â…¢) chloride was discovered highly effective as catalyst in the Friedel-Crafts reactions of electron-rich arenes with imines or aziridines,which provides a facile and convenient route for the synthesis ofβ-aryl amines.We also found that quinine as an efficient organocatalyst for enantioselective desymmetrization of meso-aziridines with benzenethiols,which gives rise to theβ-amino sulfides in high yields with moderate to good enantioselectivities.