An efficient route to 3-aryl-substituted quinolin-2-one and 1,8-naphthyridin-2-one derivatives of pharmaceutical interest.
Reaction of arylacetic ester enolates with 2-alkoxy-4H-3,1-benzoxazin-4-ones offers a short and versatile synthetic route to 3-aryl-4-hydroxyquinolin-2(1H)-ones, through the cyclization of the beta-ketoesters produced. Similar reactions of 4H-pyrido[2,3-d][1,3]oxazin-4-ones with ester enolates afford 1-acyl-4-hydroxy-1,8-naphthyridin-2(1H)-ones in a convenient two-step, one-pot procedure.
Mitsos
Christos A
CA
National Technical University of Athens, School of Chemical Engineering, Laboratory of Organic Chemistry, Zografou Campus, Greece.
Zografos
Alexandros L
AL
Igglessi-Markopoulou
Olga
O
D002384:Catalysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D009287:Naphthyridines / Q000138:chemical synthesis*; D010078:Oxazines / Q000138:chemical synthesis*; D004364:Pharmaceutical Preparations / Q000138:chemical synthesis*; D015363:Quinolones / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D009287:Naphthyridines; D010078:Oxazines; D004364:Pharmaceutical Preparations; D015363:Quinolones