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

Available for download on Friday, June 12, 2020

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