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Issue 44, 2019
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Straightforward access to complex isoindolinones from the Ugi reaction of o-nitrobenzoic acid derivatives

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Abstract

The Ugi reaction of 2-nitrobenzoic acid derivatives has been used for a diversity oriented synthesis of complex isoindolinones via a SNAr reaction involving the peptidyl position. When the cyclization is triggered by strong bases such as potassium tert-butylate, the SNAr reaction is followed by a deamidification/oxidation sequence leading to 2-hydroxyisoindolinones. The latter may be further transformed into polycyclic fused isoindolinones via Pictet–Spengler type cyclization or O-alkylation/metathesis sequences.

Graphical abstract: Straightforward access to complex isoindolinones from the Ugi reaction of o-nitrobenzoic acid derivatives

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Publication details

The article was received on 22 Sep 2019, accepted on 23 Oct 2019 and first published on 23 Oct 2019


Article type: Paper
DOI: 10.1039/C9OB02065A
Org. Biomol. Chem., 2019,17, 9655-9659

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    Straightforward access to complex isoindolinones from the Ugi reaction of o-nitrobenzoic acid derivatives

    M. Kurva, M. Dolé Kerim, R. Gàmez-Montaño and L. El Kaim, Org. Biomol. Chem., 2019, 17, 9655
    DOI: 10.1039/C9OB02065A

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