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Paper | Regular issue | Vol 43, No. 2, 1996, pp.447-461
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7316
Approach to the Synthesis of 1,5-Diazaanthraquinones by Diels-Alder Reactions of Quinoline-5,8-diones

Ricardo A. Tapia,* Carmina Quintanar, and Jaime A. Valderrama

*Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Santiago-22, Chile

Abstract

9-Hydroxy- and 6-hydroxybenzo[g]quinoline-5,10-dione (18) and (22) have been obtained through the selective Diels-Alder reaction of 1-trimethylsilyloxy-1,3-butadiene (8) with quinoline-5,8-dione (2) and tetrahydroquinoline-5,8-dione (7) respectively. The treatment of quinone (2) with 1-dimethylamino-1-aza-1,3-butadiene (9) affords a mixture of the diazaanthraquinones (23) and (24) in a 1:3.6 ratio. The synthesis of 1,5-diazaanthraquinone (26) via the reaction of quinone (7) with azadiene (9) is also described.