REACTIONS OF TRIACETIC LACTONE WITH AMINES UNDER VARIOUS CONDITIONS

Abstract

The reaction of triacetic lactone with amines was investigated previously by Prof. A.K. Kiang and others, and found to yield 3,5- dioxohexanilide (i), 4-hydroxy-6-methyl-1-phenyl-2-pyridone (II) and 4-anilino-6-methyl-1-phenyl-2-pyridone (III). A mechanism for the reaction has been suggested for the conversion of 2 pyrone to 2-pyridones, The reaction was repeated under various conditions in order to get the best condition for getting more of compound (I) and compound (III), particularly the latter, as its structure required confirmation, Similar compounds were also prepared from the reaction of triacetic lactone ' with P-nitroaniline and O-Chloroaniline using the same procedure. Other amines which failed to react with TAL were N-methylaniline, O-nitroaniline, O-phenylene diamine and hydroxyl amine, Reactions of triacetic lactone with hydrazine hydrate and with phenylhydrazine were also carried out. These gave compounds which are distinct from 2-pyridones and are believed to be derivatives of pyrazole. The structure of all the compounds studied were substantiated in moat oases by evidence from microanalysis and their NMR, infrared and ultraviolet spectra.