Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Molecules Année : 2021

Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties

Résumé

Five protocols were first compared for the copper-catalyzed C-N bond formation between 7-azaindole and aryl/heteroaryl iodides/bromides. The 1-arylated 7-azaindoles thus obtained were subjected to deprotometalation-iodolysis sequences using lithium 2,2,6,6-tetramethylpiperidide as the base and the corresponding zinc diamide as an in situ trap. The reactivity of the substrate was discussed in light of the calculated atomic charges and the pK(a) values. The behavior of the 1-arylated 7-azaindoles in direct iodination was then studied, and the results explained by considering the HOMO orbital coefficients and the atomic charges. Finally, some of the iodides generated, generally original, were involved in the N-arylation of indole. While crystallographic data were collected for fifteen of the synthesized compounds, biological properties (antimicrobial, antifungal and antioxidant activity) were evaluated for others.

Domaines

Chimie
Fichier principal
Vignette du fichier
molecules-26-06314-v2.pdf (12.45 Mo) Télécharger le fichier
Origine : Fichiers éditeurs autorisés sur une archive ouverte

Dates et versions

hal-03414634 , version 1 (04-11-2021)

Licence

Paternité

Identifiants

Citer

Mohamed Yacine Ameur Messaoud, Ghenia Bentabed-Ababsa, Ziad Fajloun, Monzer Hamze, Yury S Halauko, et al.. Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties. Molecules, 2021, 26 (20), pp.6314. ⟨10.3390/molecules26206314⟩. ⟨hal-03414634⟩
15 Consultations
13 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More