The preparation and aqueous basic oxidation of diethyl 1-methyl-3-hydroxy-5-phenylpyrrole-2,4-dicarboxylate

Autor: E. Campaigne, G. M. Shutske
Rok vydání: 1974
Předmět:
Zdroj: Journal of Heterocyclic Chemistry. 11:929-936
ISSN: 1943-5193
0022-152X
DOI: 10.1002/jhet.5570110614
Popis: 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.
Databáze: OpenAIRE
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