E. Campaigne, G. Shutske
Dec 1, 1974
Citations
0
Influential Citations
12
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
Diethyl 1-methyl-3-hydroxy-5-phenylpyrrole-2,4-dicarboxylate has been synthesized in good yield from readily available materials, diethyl benzylidenemalonate and ethyl sarcosinate. It was found to react with oxygen in aqueous base to give two oxidation products, ethyl 1-methyl-2-oxo-3-hydroxy-5-phenyl-3-pyrroline-4-carboxylate (9) and ethyl 1-methyl-2,3-dioxo-5-phenyl-4-pyrroline-4-carboxylate (10). These two oxidation products are postulated to arise from the decomposition of a common intermediate, diethyl 1-methyl-2-hydroperoxy-3-oxo-5-phenyl-4-pyrroline-2,4-dicarboxylate. Reaction of the title compound with oxygen in pyridine containing Triton B again produced two products, the dioxo compound (10) and diethyl 1-methyl-2-hydroxy-3-oxo-5-phenyl-4-pyrroline-2,4-dicarboxylate (12). Compound 12 was shown to react in aqueous base to give exclusively 9. The hydration of 10 in acidic and basic media is also discussed.