1‐Methyl‐3,6,8‐trinitro‐2‐quinolone (1) behaved as the dienophile in Diels‐Alder reactions with dienes. When cyclopentadiene was used, cycloadduct 4 was obtained, which was then aromatized on treatment with triethylamine. In the reaction of 1 with hydrazone of 2‐butenal, phenanthridine derivative 7 was produced.
Electron-deficient 1-methyl-3,6,8-trinitro-2-quinolone is highly reactive, and readily reacted with two equivalents of primary amines at room temperature to afford ammonium salts of 4-alkylamino-3,4-dihydro-1-methyl-3,6,8-trinitro-2-quinolones.4-Alkylamino-6,8-dinitro-1-methyl-2-quinolones were also prepared when the reaction was conducted at elevated temperature.
Fused pyridine derivatives R 0450 Diels-Alder Reaction of 1-Methyl-3,6,8-trinitro-2-quinolone. -(ASAHARA, M.; NAGAMATSU, M.; TOHDA, Y.; NISHIWAKI*, N.; ARIGA, M.;
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