Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties
| Autor: | Monzer Hamze, Thierry Roisnel, Ghenia Bentabed-Ababsa, Vadim E. Matulis, Mohamed Yacine Ameur Ameur Messaoud, Vincent Dorcet, Yury S. Halauko, Florence Mongin, Ziad Fajloun, Oleg A. Ivashkevich |
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| Přispěvatelé: | Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université d'Oran 1 Ahmed Ben Bella [Oran], Ecole Doctorale des Sciences et de la Technologie (EDST), Lebanese University [Beirut] (LU), Doctoral School of Sciences and Technology [Lebanese University], Belarusian State University, This research received no external funding., Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
N-arylation
Pharmaceutical Science chemistry.chemical_element Organic chemistry Zinc 010402 general chemistry 01 natural sciences Medicinal chemistry Article Analytical Chemistry chemistry.chemical_compound QD241-441 Drug Discovery iodination 7-azaindole [CHIM]Chemical Sciences Molecule Reactivity (chemistry) Physical and Theoretical Chemistry deprotometalation Indole test 010405 organic chemistry Aryl Halogenation Regioselectivity 0104 chemical sciences chemistry Chemistry (miscellaneous) regioselectivity Molecular Medicine Lithium |
| Zdroj: | Molecules, Vol 26, Iss 6314, p 6314 (2021) Molecules Molecules, MDPI, 2021, 26 (20), pp.6314. ⟨10.3390/molecules26206314⟩ Volume 26 Issue 20 Molecules, 2021, 26 (20), pp.6314. ⟨10.3390/molecules26206314⟩ |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules26206314⟩ |
| Popis: | International audience; 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. |
| Databáze: | OpenAIRE |
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