Straightforward access to complex isoindolinones from the Ugi reaction of o-nitrobenzoic acid derivatives
Mahanandaiah Kurva1, Mansour Dolé Kerim2, Rocio Gàmez-Montaño3
1Laboratoire de Synthèse Organique, CNRS, Ecole Polytechnique, ENSTA Paris, UMR 7652, Institut Polytechnique de Paris, 828 Bd des Maréchaux, 91128 Palaiseau, France. laurent.elkaim@ensta-paristech.fr mansour-dole.kerim@ensta-paris.fr and Departamento de Química, Universidad de Guanajuato, Noria Alta S/N, CP 36050 Guanajuato, Gto, Mexico. rociogm@ugto.mx.
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.
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