Synthesis of 5(6H)-phenanthridones using Diels-Alder reaction of 3-nitro-2(1H)-quinolones acting as dienophiles

Reiko Fujita; Toshiteru Yoshisuji; Sota Wakayanagi; Hideaki Wakamatsu; Hisao Matsuzaki

doi:10.1248/cpb.54.204

Synthesis of 5(6H)-phenanthridones using Diels-Alder reaction of 3-nitro-2(1H)-quinolones acting as dienophiles

Chem Pharm Bull (Tokyo). 2006 Feb;54(2):204-8. doi: 10.1248/cpb.54.204.

Authors

Reiko Fujita¹, Toshiteru Yoshisuji, Sota Wakayanagi, Hideaki Wakamatsu, Hisao Matsuzaki

Affiliation

¹ Tohoku Pharmaceutical University, Sendai, Japan. refujita@tohoku-pharm.ac.jp

PMID: 16462064
DOI: 10.1248/cpb.54.204

Abstract

Diels-Alder reactions of 3-nitro-2(1H)-quinolones with 1,3-butadiene derivatives were carried out to give the phenanthridone derivatives under both atmospheric and high pressure conditions. Furthermore, the reactivity of 3-substituted 2(1H)-quinolones acting as a dienophile with 2,3-dimethyl-1,3-butadiene was examined using molecular orbital (MO) calculation.

MeSH terms

Butadienes
Chromatography, Thin Layer
Indicators and Reagents
Magnetic Resonance Spectroscopy
Methylation
Nitro Compounds / chemical synthesis*
Phenanthridines / chemical synthesis*
Quinolones / chemical synthesis*
Spectrophotometry, Infrared

Substances

Butadienes
Indicators and Reagents
Nitro Compounds
Phenanthridines
Quinolones
1,3-butadiene