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Benzoazepine-fused isoindolines via intramolecular (3 + 2)-cycloadditions of azomethine ylides with dinitroarenes

Citation

Wales, SM and Rivinoja, DJ and Gardiner, MG and Bird, MJ and Meyer, AG and Ryan, JH and Hyland, CJT, Benzoazepine-fused isoindolines via intramolecular (3 + 2)-cycloadditions of azomethine ylides with dinitroarenes, Organic Letters, 21, (12) pp. 4703-4708. ISSN 1523-7060 (2019) [Refereed Article]

Copyright Statement

Copyright 2019 American Chemical Society

DOI: doi:10.1021/acs.orglett.9b01580

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.

Item Details

Item Type:Refereed Article
Research Division:Chemical Sciences
Research Group:Organic chemistry
Research Field:Organic chemical synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the chemical sciences
UTAS Author:Gardiner, MG (Associate Professor Michael Gardiner)
ID Code:151950
Year Published:2019
Web of Science® Times Cited:7
Deposited By:Plant Science
Deposited On:2022-08-09
Last Modified:2022-09-07
Downloads:0

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