74610-76-7Relevant articles and documents
THE α-ARYLATION OF DERIVATIVES OF MALONIC ACID WITH ARYLLEAD TRIACETATES. NEW SYNTHESES OF IBUPROFEN AND PHENOBARBITAL.
Pinhey, John T.,Rowe, Bruce A.
, p. 965 - 968 (1980)
Derivatives of Meldrum's acid and the sodium salts of substituted malonic acid esters undergo rapid arylation in high yield when treated with aryllead triacetates.These reactions have been applied to the synthesis of ibuprofen, an analgesic, and in a closely related reaction 5-ethylbarbituric acid has been reacted with phenyllead triacetate to give phenobarbital.
The Chemistry of Aryllead(IV) Tricarboxylates. Reaction with Derivatives of Malonic Acid: New Routes to α-Aryl Carboxylic Acids and Arylated Barbituric Acid Derivatives
Kopinski, Richard P.,Pinhey, John T.,Rowe, Bruce A.
, p. 1245 - 1254 (2007/10/02)
Derivatives of 2,2-dimethyl-1,3-dioxan-4,6-dione (Meldrum's acid) and the sodium salts of substituted malonic esters undergo electrophilic C-arylation in high yield with aryllead triacetates, thus providing new routes to α-arylalkanoic acids.Syntheses of the antiflammatory compound 2-(p-isobutylphenyl)propanoic acid (Ibuprofen) have been carried out to demonstrate the method.The arylation reaction has been extended to 5-ethylbarbituric acid and to barbituric acid itself, which affords the 5,5-diarylated derivatives in good yield.A study of the effect of some tertiary bases on the reaction of p-methoxyphenyllead triacetate with the 5-isopropyl derivative of Meldrum's acid has shown that replacement of pyridine by 2,2'-bipyridyl results in an increase in yield and reaction rate, while a further marked improvement occurs in the presence of 1,10-phenanthroline.
