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Carbonylation of various organolithium reagents. A novel approach to heterocycles via intramolecular trapping of aromatic acyllithiums

Smith, Keith, El-Hiti, Gamal A., Pritchard, Gareth J. and Hamilton, Anna 1999. Carbonylation of various organolithium reagents. A novel approach to heterocycles via intramolecular trapping of aromatic acyllithiums. Journal of the Chemical Society, Perkin Transactions 1 (16) , pp. 2299-2303. 10.1039/A903467F

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Abstract

Doubly lithiated N-pivaloylanilines react smoothly with carbon monoxide at 0 °C to give 3-tert-butyl-3-hydroxy-2,3-dihydroindol-2-ones in good yields. Similarly, carbonylation of doubly lithiated 4-pivaloylamino- and 2-pivaloylaminopyridines at 0 °C affords the corresponding 5-aza- and 7-aza-3-tert-butyl-3-hydroxy-2,3-dihydroindol-2-ones, respectively, in good yields. However, carbonylation of doubly lithiated N-pivaloyl-o-toluidines takes a different course due to direct intramolecular cyclisation of the dilithio reagents to afford 2-tert-butylindoles without uptake of carbon monoxide.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: RSC Publishing
ISSN: 0300-922X
Last Modified: 04 Jun 2017 02:51
URI: http://orca-mwe.cf.ac.uk/id/eprint/12698

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