A novel approach to the synthesis of 6-amino-7-hydroxy-flavone.
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.
Tang
Lijun
L
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116012, PR China.
Zhang
Shufen
S
Yang
Jinzong
J
Gao
Wentao
W
Cui
Jian
J
Zhuang
Tianyu
T
D000098:Acetophenones / Q000737:chemistry; D001565:Benzoates / Q000737:chemistry; D047309:Flavones / Q000138:chemical synthesis*
C525223:6-amino-7-hydroxy-flavone; D000098:Acetophenones; D001565:Benzoates; D047309:Flavones; C013409:benzoyl chloride