Some new routes for the preparation of 3-amino-2-phenyl-4(1H)-quinolinones from anthranilamides.
[reaction: see text] Several new routes for the preparation of 3-amino-2-phenyl-4-1(H)-quinolinone 7a are compared. The most efficient is based on the cyclization of phenacyl anthranilamide 2a in the presence of (poly)phosphoric acid. The mechanisms of the rearrangements involved are discussed on the basis of the structures of isolated heterocyclic intermediates. The best methodology for the preparation of the title compound 7a was verified, and 10 other quinolinones 7 were prepared.
Hradil
Pavel
P
Department of Organic Chemistry, Palacký University, Tr. Svobody 8, 771 46 Olomouc, Czech Republic. hradil@farmak.cz
Grepl
Martin
M
Hlavác
Jan
J
Soural
Miroslav
M
Malon
Michal
M
Bertolasi
Valerio
V