Tetrahedron

Concise preparation of 1, 8-diazaanthracene-2, 7, 9, 10-tetraones. Two alternative syntheses of the natural antifolate diazaquinomycin A

…, P López-Alvarado, E Pascual-Alfonso, C Avendaño…

Index: Perez, Jose Maria; Lopez-Alvarado, Pilar; Pascual-Alfonso, Eva; Avendano, Carmen; Menendez, J. Carlos Tetrahedron, 2000 , vol. 56, # 26 p. 4575 - 4583

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Citation Number: 28

Abstract

Treatment of compounds bearing one or two 1-dimethylamino-1, 4-dihydropyridine moieties with the urea-hydrogen peroxide complex (UHP) led to their efficient aromatization. Double N-oxidation of 1, 8-diazaanthraquinones thus obtained is the first example of a double N- oxidation of a diaza heterocycle by UHP in trifluoroacetic acid. Treatment of the crude double N-oxides with tosyl chloride in acetonitrile–water afforded 1, 8-diazaanthracene-2, ...