An effective synthesis of 5,4'-disubstituted flavones via a cesium enolate assisted intramolecular ipso-substitution reaction.
A variety of 5,4'-disubstituted flavones, which are anticipated to be androgen receptor antagonists to treat diseases mediated by the androgen receptor, were synthesized. It was found that an intramolecular ipso-substitution reaction via cesium enolate using 2-fluoro-6-hydroxyacetophenone and various benzoyl chlorides was effective in the preparation of 5-hydroxy-4'-alkylflavones.
Matsugi
Masato
M
Department of Applied Biological Chemistry, Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi,Tempaku-ku, Nagoya, Japan. matsugi@meijo-u.ac.jp
Takeda
Masaki
M
Takahashi
Ayano
A
Tazaki
Takahide
T
Tamura
Hiroto
H
Shioiri
Takayuki
T
D059002:Androgen Receptor Antagonists / Q000138:chemical synthesis / Q000737:chemistry; D002586:Cesium / Q000737:chemistry*; D047309:Flavones / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism
D059002:Androgen Receptor Antagonists; D047309:Flavones; D002586:Cesium