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Article Dans Une Revue Tetrahedron Année : 2021

Synthesis of γ-carboline N-oxide under gold(I)-catalysis and C-1 amino and fluoro γ-carboline

Résumé

Intramolecular gold (I)-catalyzed cyclization of 2-alkynylindole-3-carbaldehyde oximes enabled direct construction of the unknown γ-carboline N-oxide scaffold at ambient temperature. This reaction proceeded through an interesting 6-endo-dig mechanism and afforded the desired products with satisfactory to high yields. The scope and limitations of the methodology were evaluated and the final compounds fully characterized. From the 3-phenyl-N-oxide derivative, fluorination assays were achieved in two steps including the design of several C-1 ammonium salts and their nucleophilic displacements by fluorine to yield 1-fluoro-γ-carboline.

Domaines

Chimie
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Dates et versions

hal-03717446 , version 1 (13-06-2023)

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Paternité - Pas d'utilisation commerciale

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Zak Agnieszka, Hamid Marzag, Rodrigues Nuno, Vercouillie Johnny, Sylvie Chalon, et al.. Synthesis of γ-carboline N-oxide under gold(I)-catalysis and C-1 amino and fluoro γ-carboline. Tetrahedron, 2021, 89, pp.132154. ⟨10.1016/j.tet.2021.132154⟩. ⟨hal-03717446⟩
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