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Issue 21, 2012
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A novel approach to isoindolo[2,1-a]indol-6-ones

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Abstract

A convenient route to isoindolo[2,1-a]indol-6-ones has been developed starting from the appropriate 2-(N-phthaloyl)benzoic acids. Formation of the acid chlorides with thionyl chloride followed by heating with triethyl phosphite in a suitable solvent resulted in a multistep reaction giving tetracyclic β-ketophosphonates that on reduction with sodium borohydride gave the required indolones in good overall yields. Analogous β-ketophosphonates were also prepared starting with N,N-(1,8-naphthaloyl)-2-aminobenzoic acid and 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acids although of these only the naphthaloyl product could be reduced with sodium borohydride without cleaving the amide bond in the ring system.

Graphical abstract: A novel approach to isoindolo[2,1-a]indol-6-ones

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Publication details

The article was received on 12 Feb 2012, accepted on 02 Apr 2012 and first published on 03 Apr 2012


Article type: Paper
DOI: 10.1039/C2OB25314C
Citation: Org. Biomol. Chem., 2012,10, 4266-4279
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    A novel approach to isoindolo[2,1-a]indol-6-ones

    P. Duncanson, Y. Cheong, M. Motevalli and D. V. Griffiths, Org. Biomol. Chem., 2012, 10, 4266
    DOI: 10.1039/C2OB25314C

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