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Paper | Regular issue | Vol 57, No. 8, 2002, pp.1433-1444
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9502
A Synthesis of Oxygenated 1-Azaanthraquinones via Diels-Alder Reaction of 2,4-Dioxygenated Quinoline-5,8-diones with 1-Methoxy-3-trimethylsilyloxy-1,3-butadiene

Yoshie Horiguchi,* Noriko Fukuda, Mutsumi Takada, and Takehiro Sano

*Showa Pharmaceutical University, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan


Diels-Alder reaction of 2,4-dioxygenated quinoline-5,8-diones (7a, b and 8) with 1-methoxy-3-trimethylsilyloxy- 1,3-butadieneÅ@(11) proceeded in a regio- and stereoselctive manner to give 2,4,6,8-tetraoxygenated 1-azaanthraquinoes (12a, b and 18) in good to moderate yields, respectively. The results demonstrated that Diels-Alder reaction of the 2,4-dioxygenated quinolone-5,8-diones with the activated diene provides a useful method for synthesizing highly oxygenated 1-azaanthraquinones.