Competitive 1,3-Dipolar Cycloaddition Reactions of an Azomethine Ylide with Aromatic and Carbonyl Groups of Nitro-Substituted Isatoic Anhydrides

Authors

Asha D'Souza, CSIRO Manufacturing Flagship
Daniel Rivinoja, University of WollongongFollow
Roger Mulder, CSIRO Manufacturing Flagship
Jonathan M. White, University of Melbourne
Adam G. Meyer, CSIRO Manufacturing FlagshipFollow
Christopher J. T Hyland, University of WollongongFollow
Jack Ryan, CSIRO Manufacturing FlagshipFollow

RIS ID

130172

Publication Details

D'Souza, A. M., Rivinoja, D. J., Mulder, R. J., White, J. M., Meyer, A. G., Hyland, C. J. T. & Ryan, J. H. (2018). Competitive 1,3-Dipolar Cycloaddition Reactions of an Azomethine Ylide with Aromatic and Carbonyl Groups of Nitro-Substituted Isatoic Anhydrides. Australian Journal of Chemistry, 71 690-696.

Abstract

A study of the reactivity of a non-stabilised azomethine ylide, derived from N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine, with nitro-substituted isatoic anhydrides was undertaken. N-Methyl-4-nitroisatoic anhydride underwent a 1,3-dipolar cycloaddition reaction exclusively at the isatoic anhydride C1-carbonyl group, followed by decarboxylative rearrangement to yield a benzo-1,3-diazepin-5-one derivative. In contrast, N-methyl-5-nitroisatoic anhydride underwent competing cycloaddition processes to the isatoic anhydride C1-carbonyl group and to the nitro-substituted aromatic ring. The dearomative addition reaction resulted in the formation of novel tetracyclic products.