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

doi:10.1021/acs.orglett.9b01580

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

Journal article

Peer reviewed

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 and Christopher J. T Hyland

Organic Letters, Vol.21(12), pp.4703-4708

2019

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

PMID: 31188010

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Abstract

cyclization

hydrocarbons

monomers

peptides and proteins

reaction products

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.

Details

Title: Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes
Authors: Steven M Wales (Author) - University of Wollongong
Daniel J Rivinoja (Author) - University of Wollongong
Michael G Gardiner (Author) - University of Tasmania
Melissa J Bird (Author) - University of Wollongong
Adam G Meyer (Author) - CSIRO Manufacturing
John H Ryan (Author) - CSIRO Manufacturing
Christopher J. T Hyland (Corresponding Author) - University of Wollongong
Publication details: Organic Letters, Vol.21(12), pp.4703-4708
Publisher: American Chemical Society
DOI: 10.1021/acs.orglett.9b01580
ISSN: 1523-7052
PMID: 31188010
Organisation Unit: Student Services and Engagement; School of Science, Technology and Engineering
Language: English
Record Identifier: 99707484802621
Output Type: Journal article

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Collaboration types: Domestic collaboration
Web Of Science research areas: Chemistry, Organic

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