A novel approach to the synthesis of 6-amino-7-hydroxy-flavone

Lijun Tang; Shufen Zhang; Jinzong Yang; Wentao Gao; Jian Cui; Tianyu Zhuang

doi:10.3390/91000842

A novel approach to the synthesis of 6-amino-7-hydroxy-flavone

Molecules. 2004 Sep 30;9(10):842-8. doi: 10.3390/91000842.

Authors

Lijun Tang¹, Shufen Zhang, Jinzong Yang, Wentao Gao, Jian Cui, Tianyu Zhuang

Affiliation

¹ State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116012, PR China.

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetophenones / chemistry
Benzoates / chemistry
Flavones / chemical synthesis*

Substances

6-amino-7-hydroxy-flavone
Acetophenones
Benzoates
Flavones
benzoyl chloride