Carbonylation of Doubly Lithiated N′-Aryl-N,N-Dimethylureas: A Novel Approach to Isatins via Intramolecular Trapping of Acyllithiums

Keith Smith; Gamal A. El-Hiti; Anthony C. Hawes

doi:10.1055/s-2003-41019

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Carbonylation of Doubly Lithiated N′-Aryl-N,N-Dimethylureas: A Novel Approach to Isatins via Intramolecular Trapping of Acyllithiums

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Carbonylation of Doubly Lithiated N′-Aryl-N,N-Dimethylureas: A Novel Approach to Isatins via Intramolecular Trapping of Acyllithiums

Keith Smith, Gamal A. El-Hiti and Anthony C. Hawes

Synthesis (Stuttgart), Vol.2003(13), pp.2047-2052

18/09/2003

DOI: https://doi.org/10.1055/s-2003-41019

Abstract

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ABSTRACT Lithiation of N′-(2-bromoaryl)-N,N-dimethylureas with methyllithium and TERT-butyllithium under nitrogen in anhydrous THF at 0 °C gave doubly lithiated arylurea derivatives, which react with carbon monoxide at 0 °C to give isatins in good yields. The scope of the reaction has been demonstrated by application to the synthesis of isatin itself and four substituted isatins bearing alkyl, chloro or fluoro groups.

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Title: Carbonylation of Doubly Lithiated N′-Aryl-N,N-Dimethylureas: A Novel Approach to Isatins via Intramolecular Trapping of Acyllithiums
Creators - without role: Keith Smith
Gamal A. El-Hiti
Anthony C. Hawes
Publication Details: Synthesis (Stuttgart), Vol.2003(13), pp.2047-2052
Identifiers: 9948388608331
Academic Unit: King Saud University
Language: English
Resource Type: Journal article