Issue 6, 2015

1,3-Dipolar cycloaddition reactions of phthalic anhydrides with an azomethine ylide

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.

Graphical abstract: 1,3-Dipolar cycloaddition reactions of phthalic anhydrides with an azomethine ylide

Supplementary files

Article information

Article type
Research Article
Submitted
19 feb 2015
Accepted
09 apr 2015
First published
13 apr 2015

Org. Chem. Front., 2015,2, 705-712

Author version available

1,3-Dipolar cycloaddition reactions of phthalic anhydrides with an azomethine ylide

H. Santos, A. Distiller, A. M. D'Souza, Q. Arnoux, J. M. White, A. G. Meyer and J. H. Ryan, Org. Chem. Front., 2015, 2, 705 DOI: 10.1039/C5QO00062A

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