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
Affiliations
Mohamed Yacine Ameur Messaoud
Institut des Sciences Chimiques de Rennes–UMR 6226, University of Rennes, CNRS, ISCR, 35000 Rennes, France
Ghenia Bentabed-Ababsa
Laboratoire de Synthèse Organique Appliquée, Faculté des Sciences Exactes et Appliquées, Université d’Oran 1 Ahmed Ben Bella, BP 1524 El M’Naouer, Oran 31000, Algeria
Ziad Fajloun
Laboratory of Applied Biotechnology (LBA3B), Azm Center for Research in Biotechnology and Its Applications, EDST, Lebanese University, Tripoli 1300, Lebanon
Monzer Hamze
Laboratoire Microbiologie, Santé et Environnement, Doctoral School of Sciences and Technology, Faculty of Public Health, Lebanese University, Tripoli 1300, Lebanon
Yury S. Halauko
UNESCO Chair of Belarusian State University, 220030 Minsk, Belarus
Oleg A. Ivashkevich
Research Institute for Physico-Chemical Problems, Belarusian State University, 220030 Minsk, Belarus
Vadim E. Matulis
Research Institute for Physico-Chemical Problems, Belarusian State University, 220030 Minsk, Belarus
Thierry Roisnel
Institut des Sciences Chimiques de Rennes–UMR 6226, University of Rennes, CNRS, ISCR, 35000 Rennes, France
Vincent Dorcet
Institut des Sciences Chimiques de Rennes–UMR 6226, University of Rennes, CNRS, ISCR, 35000 Rennes, France
Florence Mongin
Institut des Sciences Chimiques de Rennes–UMR 6226, University of Rennes, CNRS, ISCR, 35000 Rennes, France
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.
