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

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KHALAFI J.; BRUCE J.M.

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Journal Paper

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Journal: Journal of Sciences, Islamic Republic of Iran Year:2002 | Volume:13 | Issue:2 Page(s): 131-139

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Title

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

Author(s)

KHALAFI J. | BRUCE J.M. | Issue Writer Certificate

Keywords

OXIDATIVE DEHYDROGENATION; 1-TETRALONES; JUGLONE; NAPHTHAZARIN; A#-HYDROXYANTHRAQUINONES; DDQ; SILVER(I) OXIDE; MANGANESE DIOXIDE

Abstract

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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APA: Copy

KHALAFI, J., & BRUCE, J.M.. (2002). OXIDATIVE DEHYDROGENATION OF 1-TETRALONES: SYNTHESIS OF JUGLONE, NAPHTHAZARIN, AND J-HYDROXYANTHRAQUINONES. JOURNAL OF SCIENCES ISLAMIC REPUBLIC OF IRAN, 13(2), 131-139. SID. https://sid.ir/paper/529993/en

Vancouver: Copy

KHALAFI J., BRUCE J.M.. OXIDATIVE DEHYDROGENATION OF 1-TETRALONES: SYNTHESIS OF JUGLONE, NAPHTHAZARIN, AND J-HYDROXYANTHRAQUINONES. JOURNAL OF SCIENCES ISLAMIC REPUBLIC OF IRAN[Internet]. 2002;13(2):131-139. Available from: https://sid.ir/paper/529993/en

IEEE: Copy

J. KHALAFI, and J.M. BRUCE, “OXIDATIVE DEHYDROGENATION OF 1-TETRALONES: SYNTHESIS OF JUGLONE, NAPHTHAZARIN, AND J-HYDROXYANTHRAQUINONES,” JOURNAL OF SCIENCES ISLAMIC REPUBLIC OF IRAN, vol. 13, no. 2, pp. 131–139, 2002, [Online]. Available: https://sid.ir/paper/529993/en

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