Publication: A new synthetic approach towards isoquinobenzazepinone and isoindolinobenzazepinone using acid-mediated cyclisation and Heck reaction
Issued Date
2009-01-03
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ISSN
00404020
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2-s2.0-56949100156
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Mahidol University
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SCOPUS
Bibliographic Citation
Tetrahedron. Vol.65, No.1 (2009), 351-356
Suggested Citation
Wong Phakhodee, Poonsakdi Ploypradith, Poolsak Sahakitpichan, Somsak Ruchirawat A new synthetic approach towards isoquinobenzazepinone and isoindolinobenzazepinone using acid-mediated cyclisation and Heck reaction. Tetrahedron. Vol.65, No.1 (2009), 351-356. doi:10.1016/j.tet.2008.10.044 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/27300
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Title
A new synthetic approach towards isoquinobenzazepinone and isoindolinobenzazepinone using acid-mediated cyclisation and Heck reaction
Abstract
Six-membered ring cyclisation of N-ethylbenzazepinone, prepared from the condensation of benzazepinone with phenethyl iodide under basic conditions, smoothly provided the corresponding product, isoquino[1,2-b][3]benzazepinone, under acid-mediated conditions. On the other hand, the attempted direct five-membered ring cyclisation using the acid-mediated conditions failed to give the 7,5 fused ring isoindolinobenzazepinone from N-benzylbenzazepinone, but the 7,6 fused ring product was instead obtained. However, five-membered ring cyclisation of N-benzylbenzazepinone could be effected efficiently by employing the Heck reaction followed by catalytic hydrogenation to furnish the desired isoindolinobenzazepinone. © 2008 Elsevier Ltd. All rights reserved.