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

Authors

Steven M. Wales, University of WollongongFollow
Daniel Rivinoja, University of WollongongFollow
Michael G. Gardiner, University of Tasmania (UTAS)
Melissa Bird, University of WollongongFollow
Adam G. Meyer, CSIRO Manufacturing FlagshipFollow
Jack Ryan, CSIRO Manufacturing FlagshipFollow
Christopher J. T Hyland, University of WollongongFollow

RIS ID

136663

Publication Details

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.

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.

Grant Number

ARC/DP180101332