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Issue 34, 2015
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Domino reactions of diazodicarbonyl compounds with α,β-unsaturated δ-amino esters: a convenient way towards 2-oxopiperidines, dihydropyridinones and isoquinolinediones

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Abstract

Thermal decomposition of a series of diazodicarbonyl compounds in the presence of α,β-unsaturated δ-amino esters and sodium hydride gives rise to a variety of nitrogenous heterocycles. The direction of these processes is highly dependent on the structure of the initial reagents giving rise to the formation of multi-functionalized 2-oxopiperidines, 5,6-dihydropyridin-2(1H)-ones or tetrahydroisoquinoline-1,6(2H,8aH)-diones. The reactions occur in domino processes involving the Wolff rearrangement of diazocarbonyl compounds, NaH-catalyzed anti-stereoselective intramolecular Michael addition to the α,β-unsaturated system of amino esters, and in some cases also cycloelimination and intramolecular Claisen condensation of the initial products formed.

Graphical abstract: Domino reactions of diazodicarbonyl compounds with α,β-unsaturated δ-amino esters: a convenient way towards 2-oxopiperidines, dihydropyridinones and isoquinolinediones

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Publication details

The article was received on 11 Jun 2015, accepted on 16 Jul 2015 and first published on 16 Jul 2015


Article type: Paper
DOI: 10.1039/C5OB01197C
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Org. Biomol. Chem., 2015,13, 9107-9117

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    Domino reactions of diazodicarbonyl compounds with α,β-unsaturated δ-amino esters: a convenient way towards 2-oxopiperidines, dihydropyridinones and isoquinolinediones

    J. J. Medvedev, M. V. Meleshina, T. L. Panikorovskii, C. Schneider and V. A. Nikolaev, Org. Biomol. Chem., 2015, 13, 9107
    DOI: 10.1039/C5OB01197C

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