Journal article
1,3-Dipolar cycloaddition reactions of phthalic anhydrides with an azomethine ylide
Hugo Santos, Amy Distiller, Asha M D'Souza, Quentin Arnoux, Jonathan M White, Adam G Meyer, John H Ryan
ORGANIC CHEMISTRY FRONTIERS | CHINESE CHEMICAL SOC | Published : 2015
DOI: 10.1039/c5qo00062a
Abstract
A series of phthalic anhydrides underwent a 1,3-dipolar cycloaddition reaction with N-benzylazomethine ylide, formed in situ from N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine and a catalytic amount of trifluoroacetic acid, to produce unstable spiro(isobenzofuran-1,5′-oxazolidin)-3-ones. The spiro-fused oxazolidines were reduced with sodium borohydride to afford 1(3H)-isobenzofuranones, which were generally isolated in moderate to high overall yields.
Grants
Funding Acknowledgements
HS, AD, AMD and QA thank CSIRO Australia for scholarships. We also thank Dr Roger Mulder, Dr Jo Cosgriff and Mr Carl Braybrook for assistance with collection and interpretation of NMR and/or MS data.