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.
Publication Details Citation
D'Souza, A., Rivinoja, D., Mulder, R., White, J. M., Meyer, A. G., Hyland, C. J., & Ryan, J. (2018). Competitive 1,3-Dipolar Cycloaddition Reactions of an Azomethine Ylide with Aromatic and Carbonyl Groups of Nitro-Substituted Isatoic Anhydrides. Faculty of Science, Medicine and Health - Papers: Part B. https://doi.org/10.1071/CH18196. Retrieved from https://ro.uow.edu.au/smhpapers1/193