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

Mahanandaiah Kurva; Mansour Dolé Kerim; Rocio Gàmez-Montaño; Laurent El Kaim

doi:10.1039/c9ob02065a

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

Mahanandaiah Kurva
, Mansour Dolé Kerim
, Rocio Gàmez-Montaño
, Laurent El Kaim

Research output: Contribution to journal › Article › peer-review

Abstract

The Ugi reaction of 2-nitrobenzoic acid derivatives has been used for a diversity oriented synthesis of complex isoindolinones via a S_NAr reaction involving the peptidyl position. When the cyclization is triggered by strong bases such as potassium tert-butylate, the S_NAr 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.

Original language	English
Pages (from-to)	9655-9659
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	17
Issue number	44
DOIs	https://doi.org/10.1039/c9ob02065a
Publication status	Published - 1 Jan 2019
Externally published	Yes

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title = "Straightforward access to complex isoindolinones from the Ugi reaction of: o -nitrobenzoic acid derivatives",

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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AU - Gàmez-Montaño, Rocio

AU - El Kaim, Laurent

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AB - 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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JO - Organic and Biomolecular Chemistry

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ER -

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

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