University of Hertfordshire

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By the same authors

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

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Original languageEnglish
Pages (from-to)4266-4279
Number of pages14
JournalOrganic & Biomolecular Chemistry
Volume10
Issue21
DOIs
Publication statusPublished - 2012

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 [small beta]-ketophosphonates that on reduction with sodium borohydride gave the required indolones in good overall yields. Analogous [small beta]-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.

ID: 9775887