Synthesis of 1-substituted 3-nitroquinolin-4(1H)-ones

Article abstract of DOI:10.1002/jhet.5570310232

A versatile synthetic method for preparing 1-substituted 3-nitroquinolin-4(1H)-ones from corresponding 2-fluoro-α-nitroacetophenones is demonstrated by the synthesis of 6,7-difluoro derivatives 7a-c. The method involves sequential treatment of the starting nitroacetophenone with triethyl orthoformate and the appropriate amine, followed by a nucleophilic cyclization reaction under mild conditions. The C-7 fluorine atom of 7 can be displaced by cyclic amines. Substituted 6-fluoro-7-(4-methy)-1-piperazinyl)-3-nitroquinolin-4(1H)-ones 8a-c were prepared in this way.