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Paper | Regular issue | Vol 53, No. 2, 2000, pp.315-322
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8765
Regioselective Synthesis of 1,5-Diazaanthraquinones via Diels-Alder Reaction of 4-Hydroxyquinolinequinone with 1-Aza-1,3-butadiene

Yoshie Horiguchi, Akio Toeda, Katsuhiro Tomoda, and Takehiro Sano*

*Showa College of Pharmaceutical Sciences, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan


Diels-Alder (D-A) reaction of 4-methoxy-2-phenylquinoline- 5,8-dione (3a) and 4-hydroxy-2-phenylquinoline-5,8-dione (3c) with 3-methyl-1-dimethylamino-1-aza-1,3-butadiene proceeded in a regioselective manner to give 4-methoxy-7-methyl-2-phenylpyrido[3,2-g]quinoline-5,10-dione (1,8-diazaanthraquinone) (7) and 4-hydroxy-8-methyl-2-phenylpyrido[2,3-g]quinoline-5,10-dione (1,5-diazaanthra-qinone) (10), respectively, after the C ring aromatization. The inverse regioselectivity observed in the case of 3c is related to the presence of the hydrogen bonding between 4-OH and 5-CO group. This result demonstrated that D-A reaction of the azadienophiles with 1-azadiene provides a method for synthesizing 1,8-diaza- and 1,5-diazaanthraquinone, respectively.