Benzoazepine-fused isoindolines via intramolecular (3 + 2)-cycloadditions of azomethine ylides with dinitroarenes
In: 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, 2019, S. 4703-4708
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Zugriff:
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.
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Benzoazepine-fused isoindolines via intramolecular (3 + 2)-cycloadditions of azomethine ylides with dinitroarenes
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| Autor/in / Beteiligte Person: | Wales, SM ; Rivinoja, DJ ; Gardiner, MG ; Bird, MJ ; Meyer, AG ; Ryan, JH ; Hyland, CJT |
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| Zeitschrift: | 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, 2019, S. 4703-4708 |
| Veröffentlichung: | Amer Chemical Soc, 2019 |
| Medientyp: | academicJournal |
| DOI: | 10.1021/acs.orglett.9b01580 |
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