title: A concise and versatile synthesis of viridicatin alkaloids from cyanoacetanilides.
abstract: 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.
authors.affiliation: Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, Sanuki-shi, Kagawa 769-2193, Japan.
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Kobayashi
authors.forename: Takashi
authors.initials: T
authors.lastname: Harayama
mesh_terms: D000083:Acetanilides / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006912:Hydroxyquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000083:Acetanilides; D000470:Alkaloids; D006912:Hydroxyquinolines; C050119:4-cyanoacetanilide; C009673:viridicatin