Enamine-Based Domino Strategy for C-Acylation/Deacetylation of Acetoacetamides: A Practical Synthesis of β-Keto Amides

Plamen Angelov*

*University of Plovdiv, Department of Organic Chemistry, 24 Tsar Asen Str., 4000 Plovdiv, Bulgaria, Email: angelovuni-plovdiv.bg

P. Angelov, Synlett, 2010, 1273-1275.

DOI: 10.1055/s-0029-1219836

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Abstract

Enamination of acetoacetamides with Boc-monoprotected ethylenediamine provides β-enamino amides, which can be acylated at the α-carbon with excellent selectivity. These C-acylated derivatives undergo domino fragmentation in acidic media to give the corresponding β-keto amides accompanied by 2-methyl-4,5-dihydro-1H-imidazole.

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Key Words

β-keto amides, enaminone, C-acylation, domino reaction, 1,3-dicarbonyl

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ID: J60-Y2010-1410