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Carbonylation of doubly lithiated N'-Aryl-N,N-dimethylureas: a novel approach to isatins via intramolecular trapping of acyllithiums

Smith, Keith, El-Hiti, Gamal A. and Hawes, Anthony C. 2003. Carbonylation of doubly lithiated N'-Aryl-N,N-dimethylureas: a novel approach to isatins via intramolecular trapping of acyllithiums. Synthesis (Stuttgart) (13) , pp. 2047-2052. 10.1055/s-2003-41019

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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.

Item Type: Article
Status: Published
Schools: Chemistry
Uncontrolled Keywords: carbonylation ; N,N-dimethylureas ; isatins ; intramolecular trapping ; positron emission tomography
Publisher: Georg Thieme Verlag
ISSN: 0039-7881
Date of First Compliant Deposit: 30 March 2016
Last Modified: 04 Jun 2017 02:51
URI: http://orca-mwe.cf.ac.uk/id/eprint/12705

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