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Note | Regular issue | Vol 51, No. 7, 1999, pp.1669-1680
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8549
A Chemical Evidence of Regiochemistry in the Diels-Alder Reaction of 4-Oxygenated Quinolinequinones with 1-Methoxy-3-trimethylsilyloxy-1,3-butadienes

Yoshie Horiguchi, Katsuhiro Tomoda, and Takehiro Sano*

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


The synthesis of four regioisomeric azaanthraquinones (4a, b and 5a, b) was achieved in a regioselective manner by the Diels-Alder reaction of 4-oxygenated 6-bromo- and 7-bromoquinolinequinones (11 and 15) with 1-methoxy-3-trimethylsilyloxy-1,3-butadiene. The results gave a chemical evidence of the regiochemistry observed in the Diels-Alder reactions of non-halogenated 4-oxyquinolinequinones (1a and 1b) which showed an inverse regioselectivity.