The BF3.OEt2 and MeSO3H-promoted reactions of phenols and ethyl phenylpropiolate to give neoflavones in 17-96% and flavones in 0-25% yield are described. In general, phenols with activating substituents favor the formation of neoflavones under both BF3.OEt2 and MeSO3H-promoted reaction conditions. Phenol and p-Chlorophenol reacted with ethyl phenylpropiolate under the MeSO3H-promoted reaction conditions to give close to 1:1 mixtures of the corresponding neoflavones and flavones.
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