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A Novel Approach to the Synthesis of 6-Amino-7-hydroxy-flavone

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Author(s): Lijun Tang | Shufen Zhang | Jinzong Yang | Wentao Gao | Jian Cui | Tianyu Zhuang

Journal: Molecules
ISSN 1420-3049

Volume: 9;
Issue: 10;
Start page: 842;
Date: 2004;
Original page

Keywords: Flavones | 4H-1-benzopyan-4-one | aminoflavones | chromones

ABSTRACT
A novel approach to the synthesis of 6-amino-7-hydroxyflavone (1) is described. Reaction in acetone of 2′,4′-dihydroxy-5′-nitroacetophenone and benzoyl chloride in the presence of potassium carbonate affords 3-benzoyl-7-hydroxy-6-nitroflavone, which is cleaved in 5% ethanolic potassium hydroxide to give 1-(2,4-dihydroxy-5-nitrophenyl)-3- phenyl-1,3-propanedione. The 1,3-diketone thus formed is then transformed into 7-hydroxy- 6-nitroflavone, followed by reduction to afford the title compound.
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