• Title/Summary/Keyword: intermediates for flavone synthesis

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Synthesis of 2-Aroyloxyacetophenones as Intermediates for Flavone Synthesis (Flavone의 합성 중간체인 2-Aroyloxyacetophenone류의 새로운 합성법)

  • Song, Gyu-Yong;Ahn, Byung-Zun
    • YAKHAK HOEJI
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    • v.38 no.1
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    • pp.1-5
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    • 1994
  • We have synthesized some 2-(2-benzyloxybenzoyloxy)-and 2-(2,6-dibenzyloxybenzoyloxy)-acetophenones as intermediates for flavone synthesis. The reaction of polyoxygenated 2-hydroxyacetophenones with 2-benzyloxybenzoic acid or 2,6-dibenzyloxybenzoic acid in the presence of dicyclohexylcarbodiimide and p-dimethylaminopyridine resulted in a good yield$(70{\sim}89%)$ of 2-(2-benzyloxybenzoyloxy)-acetophenones or 2-(2,6-dibenzyloxybenzoyloxy) acetophenones under milder conditions and in shorter time than the previous methods. This new methods using benzoic acids instead of benzoyl chlorides saves one reaction step of acid chlorination in comparision of the previous methods.

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Synthesis of Dibenzoylmethanes as Intermediates for Flavone Synthesis by a Modified Baker-Venkataraman Rearrangement

  • Song, Gyu-Yong;Ahn, Byung-Zun
    • Archives of Pharmacal Research
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    • v.17 no.6
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    • pp.434-437
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    • 1994
  • 1-Polyoxyphenyl-3-(2, 6-dioxyphenyl)propane-1, 3-diones have been synthesized as intermediates for flavone synthesis by condensation of 2-(2, 6-dioxybenzoyloxy)polyoxyacetophenone in the presence of phae transfer catalyst. The average yields of 1-polyoxyphenyl-3-phenylpropane-1, 3-diones, 1-polyoxyphenyl-3(2-benzyloxyphenyl)propane-1, 3-diones and 1-polyoxy-3-(2, 6-dibenzyloxyphenyl)propane-1, 3-dions were 79%, 74% and 71% respectively. The bulkiness of the benzyloxy groups or methyoxy gorups exerted steric hindrance and reduced the yield. Nevertheless, the yield were higher than the previously reported ones.

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