Synthesis of dibenzoylmethanes as intermediates for flavone synthesis by a modified Baker-Venkataraman rearrangement.
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 phase 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-diones were 79%, 74% and 71%, respectively. The bulkiness of the benzyloxy groups or methoxy groups exerted steric hindrance and reduced the yield. Nevertheless, the yields were higher than the previously reported ones.
D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry; D005419:Flavonoids / Q000138:chemical synthesis*; D008697:Methane / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry