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Issue 5, 2011
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A general approach to N-heterocyclic scaffolds using domino Heck–aza-Michael reactions

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Abstract

Palladium-catalyzed domino Heck–aza-Michael reactions for the synthesis of a series of C1-substituted tetrahydro-β-carbolines, tetrahydroisoquinolines and isoindolines are described. The domino process involves the initial intermolecular Heck reaction of an aryl bromide with an electron deficient alkene, followed by an intramolecular aza-Michael reaction to form the new N-heterocycle in high yield.

Graphical abstract: A general approach to N-heterocyclic scaffolds using domino Heck–aza-Michael reactions

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Publication details

The article was received on 06 Oct 2010, accepted on 11 Nov 2010 and first published on 12 Nov 2010


Article type: Paper
DOI: 10.1039/C0OB00835D
Citation: Org. Biomol. Chem., 2011,9, 1508-1515
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    A general approach to N-heterocyclic scaffolds using domino Heck–aza-Michael reactions

    D. L. Priebbenow, S. G. Stewart and F. M. Pfeffer, Org. Biomol. Chem., 2011, 9, 1508
    DOI: 10.1039/C0OB00835D

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