Synthesis of new azapolycyclic scaffolds via the domino aminolysis of dicyclopentadiene diepoxide in water

[Display omitted] •First reported synthesis of the octahydro-1H-2,5-epimino-4,7-methanoindene azapolycyclic system.•Operationally simple method using water as the solvent.•2D NMR and XRD spectra of the products were studied in detail. A convenient method is reported for the multigram scale synthesis...

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Veröffentlicht in:Tetrahedron letters 2020-07, Vol.61 (28), p.152097, Article 152097
Hauptverfasser: Palchykov, Vitalii A., Gaponova, Rita G., Omelchenko, Iryna V., Kasyan, Liliya I.
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Sprache:eng
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Zusammenfassung:[Display omitted] •First reported synthesis of the octahydro-1H-2,5-epimino-4,7-methanoindene azapolycyclic system.•Operationally simple method using water as the solvent.•2D NMR and XRD spectra of the products were studied in detail. A convenient method is reported for the multigram scale synthesis of compounds containing the novel octahydro-1H-2,5-epimino-4,7-methanoindene azapolycyclic system in good yields. This method involves the domino aminolysis of readily available dicyclopentadiene diepoxide in water at 165 °C. 2D NMR and XRD spectra of the products were studied in detail.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152097