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Note | Regular issue | Vol 78, No. 11, 2009, pp.2851-2854
Published online, 20th August, 2009
DOI: 10.3987/COM-09-11803
Regioselective Nitroalkylation of the 1-Methyl-2-quinolone Framework

Motoki Asahara, Masaki Ohtsutsumi, Masahiro Ariga, and Nagatoshi Nishiwaki*

*School of Science and Technology, Kochi University of Technology, Tosayamada-cho, Kochi, 782-8502, Japan

Abstract

Regioselective introduction of an (α-nitro)alkyl group to the 1-methyl-2-quinolone framework was performed upon treatment of 1-methyl-3,6,8-trinitro-2-quinolone with nitroalkanes in the presence of triethylamine, in which a nitronate anion attacks at the 4-position and the subsequent aromatization by elimination of nitrous acid lead to 4-(α-nitro)alkylated 6,8-dinitro-1-methyl-2-quinolones.