Synthesis of unnatural 1-methyl-2-quinolone derivatives.
Unnatural 1-methyl-2-quinolone derivatives were synthesized by regioselective C-C bond formation. When 1-methyl-3,6,8-trinitro-2-quinolone (TNQ) was treated with enamines, nucleophilic addition readily occurred at the 4-position, and succeeding hydrolysis of enamine moiety followed by elimination of nitrous acid furnished 4-acylmethyl-1-methyl-6,8-dinitro-2-quinolones. The same products could be prepared by the reaction of TNQ with ketones in the presence of triethylamine. The present reaction enabled the introduction of various kinds of acylmethyl groups substituted with alkyl, aryl or hetaryl groups.
Asahara
Motoki
M
Department of Chemistry, Osaka Kyoiku University, 4-698-1 Asahigaoka, Kashiwara, Osaka 582-8582, Japan.
Katayama
Taku
T
Tohda
Yasuo
Y
Nishiwaki
Nagatoshi
N
Ariga
Masahiro
M
D015363:Quinolones / Q000138:chemical synthesis*; D013678:Technology, Pharmaceutical / Q000379:methods*
D015363:Quinolones