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

Steven M. Wales, Daniel J. Rivinoja, Michael G. Gardiner, Melissa J. Bird, Adam G. Meyer, John H. Ryan, Christopher J.T. Hyland*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

3 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)4703-4708
Number of pages6
JournalOrganic Letters
Volume21
Issue number12
Early online date12 Jun 2019
DOIs
Publication statusPublished - 21 Jun 2019

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