Competitive 1,3-Dipolar Cycloaddition Reactions of an Azomethine Ylide with Aromatic and Carbonyl Groups of Nitro-Substituted Isatoic Anhydrides
Asha M. D’Souza A , Daniel J. Rivinoja C , Roger J. Mulder A , Jonathan M. White B , Adam G. Meyer A , Christopher J. T. Hyland C and John H. Ryan A D
+ Author Affiliations
- Author Affiliations
A CSIRO Manufacturing, Ian Wark Laboratory, Bayview Avenue, Clayton, Vic. 3168, Australia.
B School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, Vic. 3010, Australia.
C School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia.
D Corresponding author. Email: jack.ryan@csiro.au
Australian Journal of Chemistry 71(9) 690-696 https://doi.org/10.1071/CH18196
Submitted: 2 May 2018 Accepted: 11 June 2018 Published: 11 July 2018
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.
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