Issue 6, 2009
From the journal:

Organic & Biomolecular Chemistry

Preparation of 1-aryl-substituted isoindoline derivatives by sequential Morita–Baylis–Hillman and intramolecular Diels–Alder reactions†

Kristen Nicole Clary,a   Masood Parveza  and  Thomas George Back*a  

* Corresponding authors

a Department of Chemistry, University of Calgary, Calgary, AB, Canada
E-mail: tgback@ucalgary.ca
Fax: +1 (403) 289-9488
Tel: +1 (403) 220-6256

Abstract

Aldimines underwent Morita–Baylis–Hillman reactions with dienes activated by sulfonyl or nitrile groups. The N-allyl or propargyl derivatives of the products were subjected to intramolecular Diels–Alder cycloadditions to produce the corresponding partly saturated 1-arylisoindoline derivatives. The cycloadducts in the nitrile-activated N-propargyl series were aromatized by base-mediated elimination of HCN to afford 1-arylisoindolines, which were in turn oxidized to the corresponding 3-arylisoindolin-1-ones.

Graphical abstract: Preparation of 1-aryl-substituted isoindoline derivatives by sequential Morita–Baylis–Hillman and intramolecular Diels–Alder reactions

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Article information

DOI
https://doi.org/10.1039/B817954A
Article type
Paper
Submitted
13 Oct 2008
Accepted
12 Dec 2008
First published
11 Feb 2009

Org. Biomol. Chem., 2009,7, 1226-1230

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Preparation of 1-aryl-substituted isoindoline derivatives by sequential Morita–Baylis–Hillman and intramolecular Diels–Alder reactions

K. N. Clary, M. Parvez and T. G. Back, Org. Biomol. Chem., 2009, 7, 1226 DOI: 10.1039/B817954A

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