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Tandem inverse-electron-demand hetero-/retro-Diels–Alder reactions for aromatic nitrogen heterocycle synthesis

Radleigh A. A. Fostera  and  Michael C. Willis*a 
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* Corresponding authors

a Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UK
E-mail: michael.willis@chem.ox.ac.uk
Fax: +44 (0)1865 285002
Tel: +44 (0)1865 285126

Abstract

The merged inverse-electron-demand hetero-Diels–Alder (ihDA)/retro-Diels–Alder (rDA) reaction sequence can be used to rapidly synthesise highly functionalised nitrogen heteroaromatics. The reaction offers many advantages: high atom economy, high levels of regioselectivity, it rarely requires a catalyst and, in some cases, can be performed in the absence of solvent. In this tutorial review we discuss the range of commonly used dienophiles and aza-dienes for this process whilst highlighting the reactivity trends, and illustrating their applications.

Graphical abstract: Tandem inverse-electron-demand hetero-/retro-Diels–Alder reactions for aromatic nitrogen heterocycle synthesis

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Publication details

The article was received on 06 Aug 2012 and first published on 19 Oct 2012


Article type: Tutorial Review
DOI: 10.1039/C2CS35316D
Citation: Chem. Soc. Rev., 2013,42, 63-76
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    Tandem inverse-electron-demand hetero-/retro-Diels–Alder reactions for aromatic nitrogen heterocycle synthesis

    R. A. A. Foster and M. C. Willis, Chem. Soc. Rev., 2013, 42, 63
    DOI: 10.1039/C2CS35316D

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