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. (1381). OXIDATIVE DEHYDROGENATION OF 1-TETRALONES: SYNTHESIS OF JUGLONE, NAPHTHAZARIN, AND ?-HYDROXYANTHRAQUINONES. , 13(2), -.
. "OXIDATIVE DEHYDROGENATION OF 1-TETRALONES: SYNTHESIS OF JUGLONE, NAPHTHAZARIN, AND ?-HYDROXYANTHRAQUINONES". , 13, 2, 1381, -.
. (1381). 'OXIDATIVE DEHYDROGENATION OF 1-TETRALONES: SYNTHESIS OF JUGLONE, NAPHTHAZARIN, AND ?-HYDROXYANTHRAQUINONES', , 13(2), pp. -.
. OXIDATIVE DEHYDROGENATION OF 1-TETRALONES: SYNTHESIS OF JUGLONE, NAPHTHAZARIN, AND ?-HYDROXYANTHRAQUINONES. , 1381; 13(2): -.

OXIDATIVE DEHYDROGENATION OF 1-TETRALONES: SYNTHESIS OF JUGLONE, NAPHTHAZARIN, AND ?-HYDROXYANTHRAQUINONES

Journal of Sciences, Islamic Republic of Iran
مقاله 6، دوره 13، شماره 2، شهریور 2002    اصل مقاله (210.47 K)
چکیده
Treatment of 5,8-dihydroxy-1-tetralone (9) with either 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in refluxing benzene or silver (I) oxide in refluxing 1,4-dioxane afforded juglone (5-hydroxy-1,4-naphthoquinone) (1) in good yield. With manganese dioxide in dioxane the tetralone gave a mixture of juglone and naphthazarin (5,8-dihydroxy-1,4-naphthoquinone) (3), the proportion of naphthazarin being increased by the presence of water. Silver (I) oxide in 1,4-dioxane converted 9,10-dihydroxy-1-oxo (14),9,10-dihydroxy-1,5-dioxo (15), and 1,8-dioxo-1,2,3,4,5,6,7,8-octahydro anthracene (16) into, respectively, 1-hydroxy-5,6,7,8-tetrahydro (23), 1,5-dihydroxy (6), and 1,8-dihydroxy-9,10-anthraquinone (4), in high yield. Mechanisms for these transformations are discussed.
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