Diversity-Oriented Synthesis of Functionalized Quinolin-2(1H)-ones via Pd-Catalyzed Site-Selective Cross-Coupling Reactions

Biologically active 3-amino-4-arylquinolin-2(1H)-ones and 3-alkenyl-4-arylquinolin-2(1H)-ones were synthesized in an efficient and concise manner, utilizing readily available 4-hydroxyquinolin-2(1H)-one as starting material. The key steps, which introduced selectivity and diversity in the synthesis, were the palladium-catalyzed site-selective Suzuki-Miyaura/Buchwald-Hartwig amination and Suzuki-Miyaura/Heck coupling reactions of 3-bromo-4-trifloxy-quinolin-2(1H)-one.