Diels‐alder reaction of 1‐methyl‐3,6,8‐trinitro‐2‐quinolone

Abstract

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.

Recent Progress in Nitro-Promoted Direct Functionalization of Pyridones and Quinolones

“…On the contrary, 1-methyl-3,6,8-trinitro-2-quinolone 16 undergoes cycloaddition with dienes easily under mild conditions (Scheme 3). Indeed, the cycloaddition of 16 with cyclopentadiene proceeds smoothly to furnish a tetracyclic compound 17 that aromatizes via elimination of a nitrous acid in the presence of triethylamine to afford compound 18 [37]. Similarly, the cycloaddition using α,β-unsaturated oxime, instead of cyclopentadiene, as a heterodiene affords the polycyclic diazaphenanthrene 19 (Scheme 4) [38].…”

Chemistry of Nitroquinolones and Synthetic Application to Unnatural 1-Methyl-2-quinolone Derivatives

“…, at 180 °C for 5 days in o -xylene ( Scheme 11 ) [ 40 , 41 ]. Indeed, efficient cycloaddition proceeds leading to tetracyclic compounds when TNQ is allowed to react with cyclopentadiene at 80 °C ( Scheme 18 ) [ 50 ]. The cycloadduct aromatizes with elimination of nitrous acid upon treatment with triethylamine.…”

Synthesis and Characterization of Multiple Functionalized Cyclohexanone Using Diels–Alder Reaction of α-Nitrocinnamate

“…However, there have been few examples of the Diels-Alder reaction using α-carbonylated nitroalkenes [12][13][14][15][16][17][18][19] despite abundant studies on that using α-unsubstituted nitroalkenes [1, 3,4]. However, related studies of heterocyclic compounds such as coumarin [20,21], quinolone [22][23][24], pyridone [24] and pyridazine [25] possessing an α-carbonylated nitroalkene moiety as a partial structure have been reported. Accordingly, systematic studies using α-carbonylated nitroalkene can help expand the synthetic utility of the Diels-Alder reaction.…”