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Issue 16, 1999
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Carbonylation of various organolithium reagents. A novel approach to heterocycles via intramolecular trapping of aromatic acyllithiums

Keith Smith,  Gamal A. El-Hiti,  Gareth J. Pritchard  and  Anna Hamilton 

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.

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Article type: Paper
DOI: 10.1039/A903467F
Citation: J. Chem. Soc., Perkin Trans. 1, 1999,0, 2299-2303
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    Carbonylation of various organolithium reagents. A novel approach to heterocycles via intramolecular trapping of aromatic acyllithiums

    K. Smith, G. A. El-Hiti, G. J. Pritchard and A. Hamilton, J. Chem. Soc., Perkin Trans. 1, 1999, 0, 2299
    DOI: 10.1039/A903467F

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