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A Novel Approach to the Synthesis of 6-Amino-7-hydroxy-flavone
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116012, P. R. China
College of Chemistry & Chemical Engineering, Bohai University, Jinzhou, 121003, P. R. China
* Author to whom correspondence should be addressed.
Received: 8 May 2004; Accepted: 8 July 2004 / Published: 30 September 2004
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.
Keywords: Flavones; 4H-1-benzopyan-4-one; aminoflavones; chromones
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Tang, L.; Zhang, S.; Yang, J.; Gao, W.; Cui, J.; Zhuang, T. A Novel Approach to the Synthesis of 6-Amino-7-hydroxy-flavone. Molecules 2004, 9, 842-848.
Tang L, Zhang S, Yang J, Gao W, Cui J, Zhuang T. A Novel Approach to the Synthesis of 6-Amino-7-hydroxy-flavone. Molecules. 2004; 9(10):842-848.
Tang, Lijun; Zhang, Shufen; Yang, Jinzong; Gao, Wentao; Cui, Jian; Zhuang, Tianyu. 2004. "A Novel Approach to the Synthesis of 6-Amino-7-hydroxy-flavone." Molecules 9, no. 10: 842-848.