a novel approach to the synthesis of 6-amino-7-hydroxy-flavone一种新型6-amino-7-hydroxy-flavone的合成方法.pdfVIP

Molecules 2004, 9, 842-848 molecules ISSN 1420-3049 A Novel Approach to the Synthesis of 6-Amino-7-hydroxy- flavone Lijun Tang 1,2, Shufen Zhang 1,*, Jinzong Yang 1, Wentao Gao 2, Jian Cui 1 and Tianyu Zhuang 1 1 State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116012, P. R. China. Tel: (+86) 411 2 College of Chemistry Chemical Engineering, Bohai University, Jinzhou, 121003, P. R. China. * Author to whom correspondence should be addressed; e-mail: zhangshf@. 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. Introduction Flavones constitute one of the major classes of naturally occurring products. Synthesis of flavones and their derivatives have attracted considerable attention due to their significant biocidal [1-3], pharmaceutical [4-7] and antioxidant [8-10] activities. It has been observed that the presence of hydroxyl groups at position 5 or 7 is frequently required for higher biological