Bicyclic N -dihalocyclopropylamide derivatives as precursors of nitrogen-containing fused polycyclic systems - Archive ouverte HAL
Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2023

Bicyclic N -dihalocyclopropylamide derivatives as precursors of nitrogen-containing fused polycyclic systems

Veronika Šlachtová
Nicolas Casaretto
Lucie Brulíková
Yvan Six

Résumé

Examples of carbon–carbon bond-forming cyclisation reactions, involving allyl cations generated by the thermal ring-opening of halocyclopropanes, have been scarcely reported. In this contribution, we are describing the results of a study conducted with N-dihalocyclopropylamide substrates, designed as precursors of cyclic iminium intermediates that were aimed at participating in intramolecular reactions with electron-rich aromatic groups. Competitive side-reactions were identified, and access to the desired polycyclic products was carefully evaluated. The results were found to be strongly dependent on the substitution pattern of the nucleophilic aromatic moieties, as well as on the sizes of the rings of the target products. In spite of the rather moderate yields generally obtained, this approach represents a particularly short and inexpensive route to various interesting nitrogen-containing polycyclic systems, namely benzoindolizidine, benzoquinolizidine, piperidinobenzoazepane and azepanoisoquinoline compounds.
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Dates et versions

hal-04135575 , version 1 (21-06-2023)

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Veronika Šlachtová, Nicolas Casaretto, Lucie Brulíková, Yvan Six. Bicyclic N -dihalocyclopropylamide derivatives as precursors of nitrogen-containing fused polycyclic systems. Organic & Biomolecular Chemistry, 2023, 21 (31), pp.6325-6341. ⟨10.1039/D3OB00643C⟩. ⟨hal-04135575⟩
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