Collect. Czech. Chem. Commun. 2004, 69, 822-832

Utilization of Aromatic Denitrocyclization Reaction for the Synthesis of 3-Unsubstituted 1,4-Dihydroquinolin-4-one Derivatives

Stanislav Rádl* and Iva Obadalová

Research Institute of Pharmacy and Biochemistry, U kabelovny 130, 102 37 Prague 10, Czech Republic


Synthesis of 3-unsubstituted 1-alkyl- and 1-aryl-1,4-dihydroquinolin-4-ones from 2-nitroacetophenone via the corresponding 3-amino-1-(2-nitrophenyl)prop-2-en-1-ones and -but-2-en-1-ones by denitrocyclization reaction is described. The nucleophilic cyclization was achieved either by sodium hydride or potassium carbonate in DMF.

Keywords: Enaminones; Quinolines; Ketones; Quinolin-4-ones; Aromatic denitrocyclization; Cyclizations.

References: 57 live references.