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

doi:10.1039/c9ob02065a

Paper

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

Published Nov 13, 2019 · Mahanandaiah Kurva, Mansour Dolé Kerim, Rocío Gámez-Montaño

Organic & biomolecular chemistry

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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.

Study Snapshot

The Ugi reaction of 2-nitrobenzoic acid derivatives allows for the diverse synthesis of complex isoindolinones, which can be transformed into polycyclic fused isoindolinones via Pictet-Spengler cyclization or O-alkylation/metathesis sequence

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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References

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Base-promoted cascade reaction efficiently synthesizes substituted 3-hydroxyisoindolinones under transition-metal-free conditions, with up to 93% yield for 28 examples.

To each his own: isonitriles for all flavors. Functionalized isocyanides as valuable tools in organic synthesis.

Functionalized isocyanides offer valuable tools in organic synthesis by adjusting the reactivity of the isocyano group, offering potential for new synthetic approaches.

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2-bromo-6-isocyanopyridine is an optimal convertible isocyanide for multicomponent chemistry, offering stability and synthetic efficiency, with potential applications in efficient two-step synthesis of carfentanil.

Citations

Total Synthesis of (±)-Impatien A via Aza-Heck Cyclization.

This study demonstrates the first total synthesis of impatien A using aza-Heck cyclization, enabling the complex spirocyclic ring system in seven steps from known compounds.

Pd-catalyzed post-Ugi intramolecular cyclization to the synthesis of isoquinolone-pyrazole hybrid pharmacophores & discover their antimicrobial and DFT studies

This study successfully synthesized isoquinolone-pyrazole hybrid pharmacophores with good antimicrobial activity, demonstrating potential as new antibiotics.

Synthesis of isoindolo[1,2-a]isoquinoline and isoindolo[2,1-a]quinoline derivatives via trifluoroacetic acid-mediated cascade reactions

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3-hydroxyisoindolinones can be synthesized using electrochemical, photochemical, and thermal reactions, and then used in stereoselective catalytic transformations to prepare chiral 3-substituted isoindolinone derivatives.

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