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SYNTHESIS OF SUBSTITUTED 4-(METHOXYPHENYL)-3,4-DIHYDROCOUMARINS
Chenault, Jacques,Dupin, Jean-Francois E.
, p. 437 - 443 (2007/10/02)
In polyphosphoric acid (PPA), 2- and 4-methoxycinnamic acids react with various dimethylphenols to give 4-phenyl-3,4-dihydrocoumarins by direct cycloaddition, whereas 3-methoxycinnamic acid, in the same conditions, also gives a flavanone formed by Fries rearrangement from a hydroxychalcone.These results are discussed in terms of electronic effects due to the methoxy substituents on the cinnamic acid.
