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.
Wang
Zhiyong
Z
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, P. R. China.
Wang
Bing
B
Wu
Jie
J
D002384:Catalysis; D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D010165:Palladium / Q000737:chemistry*; D015363:Quinolones / Q000138:chemical synthesis*; D021241:Spectrometry, Mass, Electrospray Ionization
D015363:Quinolones; D010165:Palladium