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Benzoazepine-fused isoindolines via intramolecular (3 + 2)-cycloadditions of azomethine ylides with dinitroarenes
journal contribution
posted on 2023-05-21, 11:08 authored by Wales, SM, Rivinoja, DJ, Michael GardinerMichael Gardiner, Bird, MJ, Meyer, AG, Ryan, JH, Hyland, CJTAminobenzaldehydes 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.
History
Publication title
Organic LettersVolume
21Issue
12Pagination
4703-4708ISSN
1523-7060Department/School
School of Natural SciencesPublisher
Amer Chemical SocPlace of publication
1155 16Th St, Nw, Washington, USA, Dc, 20036Rights statement
Copyright © 2019 American Chemical SocietyRepository Status
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