Synthesis of 1-Hydroxy-2-(Prop-2'-Enyl) 9-Antrone

Document Type: Research Article


Department of Chemistry, Shiraz University, Shiraz, I.R. IRAN


An efficient synthesis of the 1-hydroxy-2-(prop-2'-enyl)9-anthrone is described. Selective nitration of anthraquinone, reduction to the corresponding amine, diazotization and treatment by sulfuric acid solution afforded the 1-hydroxy-9,10-anthraquinone in good yield as the key intermediate. Reaction with allyl bromide/K2CO3 and subsequent selective reduction accompanied by a Claisen rearrangement produced the title compound in high yield.


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