Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties
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 c...
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| Format: | Article |
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MDPI AG
2021-10-01
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| Online Access: | https://www.mdpi.com/1420-3049/26/20/6314 |
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| author | 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 |
| author_facet | 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 |
| author_sort | Mohamed Yacine Ameur Messaoud |
| collection | DOAJ |
| description | 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 p<i>K</i><sub>a</sub> 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 <i>N</i>-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. |
| first_indexed | 2024-03-10T06:19:52Z |
| format | Article |
| id | doaj.art-209131335d8d4e37a85f7f836ee97bcb |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T06:19:52Z |
| publishDate | 2021-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-209131335d8d4e37a85f7f836ee97bcb2023-11-22T19:21:24ZengMDPI AGMolecules1420-30492021-10-012620631410.3390/molecules26206314Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule PropertiesMohamed Yacine Ameur Messaoud0Ghenia Bentabed-Ababsa1Ziad Fajloun2Monzer Hamze3Yury S. Halauko4Oleg A. Ivashkevich5Vadim E. Matulis6Thierry Roisnel7Vincent Dorcet8Florence Mongin9Institut des Sciences Chimiques de Rennes–UMR 6226, University of Rennes, CNRS, ISCR, 35000 Rennes, FranceLaboratoire de Synthèse Organique Appliquée, Faculté des Sciences Exactes et Appliquées, Université d’Oran 1 Ahmed Ben Bella, BP 1524 El M’Naouer, Oran 31000, AlgeriaLaboratory of Applied Biotechnology (LBA3B), Azm Center for Research in Biotechnology and Its Applications, EDST, Lebanese University, Tripoli 1300, LebanonLaboratoire Microbiologie, Santé et Environnement, Doctoral School of Sciences and Technology, Faculty of Public Health, Lebanese University, Tripoli 1300, LebanonUNESCO Chair of Belarusian State University, 220030 Minsk, BelarusResearch Institute for Physico-Chemical Problems, Belarusian State University, 220030 Minsk, BelarusResearch Institute for Physico-Chemical Problems, Belarusian State University, 220030 Minsk, BelarusInstitut des Sciences Chimiques de Rennes–UMR 6226, University of Rennes, CNRS, ISCR, 35000 Rennes, FranceInstitut des Sciences Chimiques de Rennes–UMR 6226, University of Rennes, CNRS, ISCR, 35000 Rennes, FranceInstitut des Sciences Chimiques de Rennes–UMR 6226, University of Rennes, CNRS, ISCR, 35000 Rennes, FranceFive 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 p<i>K</i><sub>a</sub> 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 <i>N</i>-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.https://www.mdpi.com/1420-3049/26/20/63147-azaindoledeprotometalationiodinationregioselectivity<i>N</i>-arylation |
| spellingShingle | 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 Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties Molecules 7-azaindole deprotometalation iodination regioselectivity <i>N</i>-arylation |
| title | Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties |
| title_full | Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties |
| title_fullStr | Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties |
| title_full_unstemmed | Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties |
| title_short | Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties |
| title_sort | deprotometalation iodolysis and direct iodination of 1 arylated 7 azaindoles reactivity studies and molecule properties |
| topic | 7-azaindole deprotometalation iodination regioselectivity <i>N</i>-arylation |
| url | https://www.mdpi.com/1420-3049/26/20/6314 |
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