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

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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

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Publication details

The article was received on 30 Oct 2018, accepted on 30 Nov 2018 and first published on 07 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02683A
Citation: Org. Biomol. Chem., 2019, Advance Article
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    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, Advance Article , DOI: 10.1039/C8OB02683A

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