Molecules (Oct 2021)

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

  • Mohamed Yacine Ameur Messaoud,
  • Ghenia Bentabed-Ababsa,
  • Ziad Fajloun,
  • Monzer Hamze,
  • Yury S. Halauko,
  • Oleg A. Ivashkevich,
  • Vadim E. Matulis,
  • Thierry Roisnel,
  • Vincent Dorcet,
  • Florence Mongin

DOI
https://doi.org/10.3390/molecules26206314
Journal volume & issue
Vol. 26, no. 20
p. 6314

Abstract

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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 pKa 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.

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