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

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A novel approach to isoindolo[2,1-a]indol-6-ones. / Duncanson, Philip; Cheong, Yuen-Ki; Motevalli, Majid; Griffiths, D. Vaughan.

In: Organic & Biomolecular Chemistry, Vol. 10, No. 21, 2012, p. 4266-4279.

Research output: Contribution to journalArticlepeer-review

Harvard

Duncanson, P, Cheong, Y-K, Motevalli, M & Griffiths, DV 2012, 'A novel approach to isoindolo[2,1-a]indol-6-ones', Organic & Biomolecular Chemistry, vol. 10, no. 21, pp. 4266-4279. https://doi.org/10.1039/C2OB25314C

APA

Vancouver

Author

Duncanson, Philip ; Cheong, Yuen-Ki ; Motevalli, Majid ; Griffiths, D. Vaughan. / A novel approach to isoindolo[2,1-a]indol-6-ones. In: Organic & Biomolecular Chemistry. 2012 ; Vol. 10, No. 21. pp. 4266-4279.

Bibtex

@article{14e79eca330e4d4899083c79ed146084,
title = "A novel approach to isoindolo[2,1-a]indol-6-ones",
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.",
author = "Philip Duncanson and Yuen-Ki Cheong and Majid Motevalli and Griffiths, {D. Vaughan}",
year = "2012",
doi = "10.1039/C2OB25314C",
language = "English",
volume = "10",
pages = "4266--4279",
journal = "Organic & Biomolecular Chemistry",
issn = "1477-0520",
publisher = "The Royal Society of Chemistry",
number = "21",

}

RIS

TY - JOUR

T1 - A novel approach to isoindolo[2,1-a]indol-6-ones

AU - Duncanson, Philip

AU - Cheong, Yuen-Ki

AU - Motevalli, Majid

AU - Griffiths, D. Vaughan

PY - 2012

Y1 - 2012

N2 - 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.

AB - 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.

U2 - 10.1039/C2OB25314C

DO - 10.1039/C2OB25314C

M3 - Article

VL - 10

SP - 4266

EP - 4279

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1477-0520

IS - 21

ER -