ChemInform Abstract: THE CHEMISTRY OF ARYLLEAD(IV) TRICARBOXYLATES. REACTION WITH DERIVATIVES OF MALONIC ACID: NEW ROUTES TO α-ARYL CARBOXYLIC ACIDS AND ARYLATED BARBITURIC ACID DERIVATIVES

Autor: B. A. Rowe, R. P. Kopinski, J. T. Pinhey
Rok vydání: 1984
Předmět:
Zdroj: Chemischer Informationsdienst. 15
ISSN: 0009-2975
DOI: 10.1002/chin.198444101
Popis: 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 providingnew 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 reactionhas 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 there action 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.
Databáze: OpenAIRE