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Access to New 2-Oxofuro[2,3-b]pyrroles and 2-Methylenepyrroles through the Reaction of 1,2-Diaza-1,3-butadienes and γ-Ketoesters
journal contribution
posted on 2004-04-16, 00:00 authored by Orazio A. Attanasi, Lucia De Crescentini, Gianfranco Favi, Paolino Filippone, Fabio Mantellini, Stefania SanteusanioNew and interesting 2-oxofuro[2,3-b]pyrroles and 19-methyl-15-oxa-20-azatricyclo[12.3.3.01,14]icos-18-en-18-carboxylates have been obtained in good yields by the one-pot reaction, in basic medium,
of 1,2-diaza-1,3-butadienes with diethyl or dimethyl acetylsuccinate or methyl 2-(1,3-dioxo-2-cyclotetradecyl)acetate, respectively, under mild conditions. Treatment of the same starting
materials with diethyl 2-acetylglutarate, in acidic medium, afforded unknown 2-methylenepyrrole
derivatives in high yields. Novel 4-(3-oxopropyl)-2,5-dimethyl-1H-pyrrole-3-carboxylates also have
been achieved by reacting 1,2-diaza-1,3-butadienes with ethyl or methyl 4-acetyl-5-oxo-hexanoate.