2-Hydroxyindoline-3-triethylammonium Bromide: A Reagent for Formal C3-Electrophilic Reactions of Indoles.

doi:10.1021/acs.orglett.7b01940

Paper

2-Hydroxyindoline-3-triethylammonium Bromide: A Reagent for Formal C3-Electrophilic Reactions of Indoles.

Published Aug 1, 2017 · Takumi Abe, Takuro Suzuki, M. Anada

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33

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Abstract

A novel indole-2,3-epoxide equivalent, 2-hydroxyindoline-3-triethylammonium bromide, was found to be a convenient reagent for formal C3-electrophilic reactions of indoles with various nucleophiles. By taking advantage of the nucleophilic character of the oxygen of the 2-hydroxyindoline, the interrupted retro-Claisen and interrupted Feist-Bénary reactions with 1,3-dicarbonyl compounds were efficiently achieved.

Study Snapshot

2-Hydroxyindoline-3-triethylammonium bromide is a convenient reagent for efficient formal C3-electrophilic reactions of indoles with various nucleophiles.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

2-Hydroxyindoline-3-triethylammonium Bromide: A Reagent for Formal C3-Electrophilic Reactions of Indoles.

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References

Citations

Recent Developments in Stereoselective Reactions of Sulfoxonium Ylides

Recent developments in sulfoxonium ylide chemistry have led to the development of novel stereoselective methodologies using organocatalysis and transition metal catalysis.

Facile Synthesis of Indolin‐2,3‐Acetonide Derivatives as Indoxyl Precursors and Protected Compounds of Indoles

Indolin2,3-acetonide derivatives are easy to handle, stable, and can serve as protected indole compounds, enabling the synthesis of indoxyl derivatives from protected indoles.

Interrupted Plancher Rearrangement Initiated by Dearomative Epoxide-Indole Cyclization: Formal Umpolung Reactivity of Indoles.

The interrupted Plancher rearrangement enables the rapid synthesis of new fused-bridged indolines with high yields and full regio- and diastereocontrol.

Indoline hemiaminals: a platform for accessing anthranilic acid derivatives through oxidative deformylation.

Indoline hemiaminals provide a simple synthetic method for accessing decorated 2-aminobenzoyl derivatives without transition metals, acid chlorides, or specific reagents.

Formal One Carbon Deletion of Indoline Hemiaminals under Tautomeric Control to Access 2-Aminobenzyl Compounds.

Tert-BuOK-mediated one carbon deletion of indoline hemiaminals enables efficient construction of 2-aminobenzyl compounds with high chemoselectivity, offering a new synthetic tool for functionalized compounds.