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

作者:Duncanson Philip; Cheong Yuen Ki; Motevalli Majid; Griffiths D Vaughan*
来源:ORGANIC %26 BIOMOLECULAR CHEMISTRY, 2012, 10(21): 4266-4279.
DOI:10.1039/c2ob25314c

摘要

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

  • 出版日期2012