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

N Spiccia, J Basutto, P Jokisz, LSM Wong…

Index: D'Souza, Asha M.; Spiccia, Nadia; Basutto, Jose; Jokisz, Pawel; Wong, Leon S.-M.; Meyer, Adam G.; Holmes, Andrew B.; White, Jonathan M.; Ryan, John H. Organic Letters, 2011 , vol. 13, # 3 p. 486 - 489

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Citation Number: 27

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 ...