An Effective Synthesis of 5,4'-Disubstituted Flavones via a Cesium Enolate Assisted Intramolecular ipso-Substitution Reaction

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  • Matsugi Masato
    Department of Applied Biological Chemistry, Faculty of Agriculture, Meijo University
  • Takeda Masaki
    Department of Applied Biological Chemistry, Faculty of Agriculture, Meijo University
  • Takahashi Ayano
    Department of Applied Biological Chemistry, Faculty of Agriculture, Meijo University
  • Tazaki Takahide
    Department of Applied Biological Chemistry, Faculty of Agriculture, Meijo University
  • Tamura Hiroto
    Department of Applied Biological Chemistry, Faculty of Agriculture, Meijo University
  • Shioiri Takayuki
    Department of Applied Biological Chemistry, Faculty of Agriculture, Meijo University

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Abstract

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.

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