Issue 7, 1976

Mechanistic studies in the chemistry of urea. Part I. Reaction with pentane-2,4-dione (acetylacetone)

Abstract

Urea, methylurea, and NN′-dimethylurea react with pentane-2,4-dione in acidic solution to give hydroxypyrimidines (pyrimidones). Kinetic and spectral evidence suggests that the mechanism of reaction is acid-catalysed attack of urea on the keto–enol form of pentane-2,4-dione followed by cyclisation. This is confirmed by examination of the reactions of 1,1,1-trifluoro- and 1,1,1,5,5,5-hexafluoro-pentane-2,4-dione with methylurea. Absence of an enolizable hydrogen at the 3-position in pentane-2,4-dione completely changes the course of the reaction.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1976, 832-835

Mechanistic studies in the chemistry of urea. Part I. Reaction with pentane-2,4-dione (acetylacetone)

A. R. Butler and E. Leitch, J. Chem. Soc., Perkin Trans. 2, 1976, 832 DOI: 10.1039/P29760000832

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