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

Journal Article


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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.

UOW Authors


  •   D'Souza, Asha (external author)
  •   Rivinoja, Daniel (external author)
  •   Mulder, Roger (external author)
  •   White, Jonathan M. (external author)
  •   Meyer, Adam G. (external author)
  •   Hyland, Christopher
  •   Ryan, Jack H. (external author)

Publication Date


  • 2018

Citation


  • 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.

Scopus Eid


  • 2-s2.0-85052790198

Ro Full-text Url


  • https://ro.uow.edu.au/cgi/viewcontent.cgi?article=1196&context=smhpapers1

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers1/193

Number Of Pages


  • 6

Start Page


  • 690

End Page


  • 696

Volume


  • 71

Place Of Publication


  • Australia

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.

UOW Authors


  •   D'Souza, Asha (external author)
  •   Rivinoja, Daniel (external author)
  •   Mulder, Roger (external author)
  •   White, Jonathan M. (external author)
  •   Meyer, Adam G. (external author)
  •   Hyland, Christopher
  •   Ryan, Jack H. (external author)

Publication Date


  • 2018

Citation


  • 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.

Scopus Eid


  • 2-s2.0-85052790198

Ro Full-text Url


  • https://ro.uow.edu.au/cgi/viewcontent.cgi?article=1196&context=smhpapers1

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers1/193

Number Of Pages


  • 6

Start Page


  • 690

End Page


  • 696

Volume


  • 71

Place Of Publication


  • Australia