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Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes

Journal Article


Abstract


  • Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.

UOW Authors


  •   Wales, Steven M. (external author)
  •   Rivinoja, Daniel (external author)
  •   Gardiner, Michael G. (external author)
  •   Bird, Melissa (external author)
  •   Meyer, Adam G. (external author)
  •   Ryan, Jack H. (external author)
  •   Hyland, Christopher

Publication Date


  • 2019

Citation


  • Wales, S. M., Rivinoja, D. J., Gardiner, M. G., Bird, M. J., Meyer, A. G., Ryan, J. H. & Hyland, C. J.T. (2019). Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes. Organic Letters, 21 (12), 4703-4708.

Scopus Eid


  • 2-s2.0-85067656823

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers1/786

Number Of Pages


  • 5

Start Page


  • 4703

End Page


  • 4708

Volume


  • 21

Issue


  • 12

Place Of Publication


  • United States

Abstract


  • Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.

UOW Authors


  •   Wales, Steven M. (external author)
  •   Rivinoja, Daniel (external author)
  •   Gardiner, Michael G. (external author)
  •   Bird, Melissa (external author)
  •   Meyer, Adam G. (external author)
  •   Ryan, Jack H. (external author)
  •   Hyland, Christopher

Publication Date


  • 2019

Citation


  • Wales, S. M., Rivinoja, D. J., Gardiner, M. G., Bird, M. J., Meyer, A. G., Ryan, J. H. & Hyland, C. J.T. (2019). Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes. Organic Letters, 21 (12), 4703-4708.

Scopus Eid


  • 2-s2.0-85067656823

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers1/786

Number Of Pages


  • 5

Start Page


  • 4703

End Page


  • 4708

Volume


  • 21

Issue


  • 12

Place Of Publication


  • United States