Organic Letters 2011-02-04

1,3-Dipolar cycloaddition-decarboxylation reactions of an azomethine ylide with isatoic anhydrides: formation of novel benzodiazepinones.

Asha M D'Souza, Nadia Spiccia, Jose Basutto, Pawel Jokisz, Leon S-M Wong, Adam G Meyer, Andrew B Holmes, Jonathan M White, John H Ryan

Index: Org. Lett. 13(3) , 486-9, (2011)

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Abstract

A nonstabilized azomethine ylide reacts with a wide range of substituted isatoic anhydrides to afford novel 1,3-benzodiazepin-5-one derivatives, which are generally isolated in high yield. The transformations involve 1,3-dipolar cycloaddition reactions of the ylide with the anhydrides to give transient, and in a representative case spectroscopically observable, oxazolidine intermediates that undergo ring-opening-decarboxylation-ring-closing reaction cascades to yield the 1,3-benzodiazepin-5-one products.