Issue 5, 2011
From the journal:

Organic & Biomolecular Chemistry

A general approach to N-heterocyclic scaffolds using domino Heck–aza-Michael reactions†

Daniel L. Priebbenow,a   Scott G. Stewartb  and  Frederick M. Pfeffer*a  

* Corresponding authors

a School of Life and Environmental Sciences, Deakin University, Geelong, Victoria, Australia
E-mail: fred.pfeffer@deakin.edu.au
Fax: +61 3 5227 1040
Tel: +61 3 5227 1439

b School of Biomedical, Biomolecular and Chemical Sciences, University of Western Australia, Crawley, Western Australia, Australia
E-mail: sgs@cyllene.uwa.edu.au
Fax: +61 8 6488 1005
Tel: +61 8 6488 3180

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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Article information

DOI
https://doi.org/10.1039/C0OB00835D
Article type
Paper
Submitted
06 Oct 2010
Accepted
11 Nov 2010
First published
12 Nov 2010

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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