Issue 1, 2019

Intramolecular trapping of ammonium ylides with N-benzoylbenzotriazoles in aqueous medium: direct access to the pseudoindoxyl scaffold

Abstract

The present work documents an operationally simple, clean and practical method for accessing the 2,2-disubstituted indolin-3-one (pseudoindoxyl) scaffold. The rhodium carbenoid mediated reaction between N-o-alkylamino benzoylbenzotriazoles and aryl diazoacetates occurs smoothly in water and exploits the leaving group ability of the benzotriazole moiety to install the carbonyl function in the product. Other highlights of the methodology are a wide substrate scope and experimental practicality given the re-use of the benzotriazole byproduct for starting material preparation.

Graphical abstract: Intramolecular trapping of ammonium ylides with N-benzoylbenzotriazoles in aqueous medium: direct access to the pseudoindoxyl scaffold

Supplementary files

Article information

Article type
Paper
Submitted
30 Հկտ 2018
Accepted
30 Նյմ 2018
First published
07 Դկտ 2018

Org. Biomol. Chem., 2019,17, 135-139

Intramolecular trapping of ammonium ylides with N-benzoylbenzotriazoles in aqueous medium: direct access to the pseudoindoxyl scaffold

L. Devi, R. Shukla and N. Rastogi, Org. Biomol. Chem., 2019, 17, 135 DOI: 10.1039/C8OB02683A

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