Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 17, Issue 44, Pages 9655-9659Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9ob02065a
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Funding
- CONACYT [632715/338546, 285622 CB-2016-28562]
- Laboratorio Nacional de Caracterizacion de Propiedades Fisicoquimicas y Estructura Molecular (CONACYT-Mexico) [123732]
- ENSTA Paris
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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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