α' and γ-dianions of acyclic β-(monoalkylamino)-α,β-unsaturated ketones can attack the double bond of nitroalkenes affording γ- and ε-nitro-β-enantioketones in good to high yields. In contrast to the corresponding 1,3-dicarbonyl dianions, cyclic products from intramoelcular Henry reactions are never observed. Quenching the reaction with sulphuric acid ε-nitro-β-enaminoketones are converted in low yields into dihydropyrroles.

The Reaction of the Dianion of β-Enaminoketones with Electrophiles. Part 6. Synthesis of gamma'- and epsilon-Nitro-β-enaminoketones

DE NINO, Antonio;DALPOZZO R;
1994

Abstract

α' and γ-dianions of acyclic β-(monoalkylamino)-α,β-unsaturated ketones can attack the double bond of nitroalkenes affording γ- and ε-nitro-β-enantioketones in good to high yields. In contrast to the corresponding 1,3-dicarbonyl dianions, cyclic products from intramoelcular Henry reactions are never observed. Quenching the reaction with sulphuric acid ε-nitro-β-enaminoketones are converted in low yields into dihydropyrroles.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/20.500.11770/137569
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