A concise and versatile synthesis of viridicatin alkaloids from cyanoacetanilides.
The efficient synthesis of 3-hydroxy-4-arylquinolin-2(1H)-ones through one-pot Knoevenagel condensation/epoxidation of cyanoacetanilides followed by decyanative epoxide-arene cyclization is described. A convergent assembly with functionalized aldehydes allows for rapid synthesis with diverse substitution patterns. Isolation of 3-hydroxy-4-arylquinolin-2(1H)-ones is readily accomplished by precipitation and filtration.
Kobayashi
Yusuke
Y
Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, Sanuki-shi, Kagawa 769-2193, Japan.
Harayama
Takashi
T
D000083:Acetanilides / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006912:Hydroxyquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D000083:Acetanilides; D000470:Alkaloids; D006912:Hydroxyquinolines; C050119:4-cyanoacetanilide; C009673:viridicatin