Wong PhakhodeePoonsakdi PloypradithPoolsak SahakitpichanSomsak RuchirawatChulabhorn Research InstituteMahidol UniversityThe Institute of Science and Technology for Research and Development, Mahidol University2018-09-132018-09-132009-01-03Tetrahedron. Vol.65, No.1 (2009), 351-356004040202-s2.0-56949100156https://repository.li.mahidol.ac.th/handle/20.500.14594/27300Six-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.Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemistryPharmacology, Toxicology and PharmaceuticsArticleSCOPUS10.1016/j.tet.2008.10.044