Aromatic Iodides: Synthesis and Conversion to Heterocycles
Aromatic heterocycles can be found in many molecules endowed with specific properties, in particular for applications in the fields of medicinal chemistry and materials science. In this group, we notably develop synthetic methodologies to selectively introduce iodine onto aromatic compounds and to u...
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MDPI AG
2022-11-01
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| author | Florence Mongin William Erb Frédéric Lassagne |
| author_facet | Florence Mongin William Erb Frédéric Lassagne |
| author_sort | Florence Mongin |
| collection | DOAJ |
| description | Aromatic heterocycles can be found in many molecules endowed with specific properties, in particular for applications in the fields of medicinal chemistry and materials science. In this group, we notably develop synthetic methodologies to selectively introduce iodine onto aromatic compounds and to use this heavy halogen in order to build heterocycles of interest. While we sometimes employed direct iodinations on electron-enriched aromatic compounds, we mainly optimized deprotometallation–iodolysis sequences to functionalize substrates sensitive to nucleophilic attacks. In particular, hindered lithium amide–metal trap tandems have been designed to overcome the low tolerance of some functional groups (e.g., ketones or sensitive diazines) toward organolithiums. The aromatic iodides generated in these ways have been involved in transition metal–catalyzed cross-couplings to access original scaffolds (oxazoloquinoxalines, pyrazinoisatins, pyrazinocarbazoles, etc.). We specifically developed the use of aromatic iodides in the copper-mediated <i>N</i>-arylation of anilines, e.g., to reach triarylamines. Combined with subsequent cyclizations, these reactions allowed access to numerous heterocyclic compounds (such as acridones, acridines, other aza-aromatic polycycles and helicene-like structures) with potential applications. From some of the scaffolds obtained, biological evaluation in the frame of collaborations allowed properties of interest to be discovered (e.g., specific inhibition of protein kinases GSK-3 or PIM, related to cancer development). |
| first_indexed | 2024-03-11T02:37:47Z |
| format | Article |
| id | doaj.art-545586bb0ba74291b3b2b883b7f12dca |
| institution | Directory Open Access Journal |
| issn | 2673-4583 |
| language | English |
| last_indexed | 2024-03-11T02:37:47Z |
| publishDate | 2022-11-01 |
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| spelling | doaj.art-545586bb0ba74291b3b2b883b7f12dca2023-11-18T09:47:55ZengMDPI AGChemistry Proceedings2673-45832022-11-011212010.3390/ecsoc-26-13641Aromatic Iodides: Synthesis and Conversion to HeterocyclesFlorence Mongin0William Erb1Frédéric Lassagne2Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)—UMR 6226, F-35000 Rennes, FranceUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)—UMR 6226, F-35000 Rennes, FranceUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)—UMR 6226, F-35000 Rennes, FranceAromatic heterocycles can be found in many molecules endowed with specific properties, in particular for applications in the fields of medicinal chemistry and materials science. In this group, we notably develop synthetic methodologies to selectively introduce iodine onto aromatic compounds and to use this heavy halogen in order to build heterocycles of interest. While we sometimes employed direct iodinations on electron-enriched aromatic compounds, we mainly optimized deprotometallation–iodolysis sequences to functionalize substrates sensitive to nucleophilic attacks. In particular, hindered lithium amide–metal trap tandems have been designed to overcome the low tolerance of some functional groups (e.g., ketones or sensitive diazines) toward organolithiums. The aromatic iodides generated in these ways have been involved in transition metal–catalyzed cross-couplings to access original scaffolds (oxazoloquinoxalines, pyrazinoisatins, pyrazinocarbazoles, etc.). We specifically developed the use of aromatic iodides in the copper-mediated <i>N</i>-arylation of anilines, e.g., to reach triarylamines. Combined with subsequent cyclizations, these reactions allowed access to numerous heterocyclic compounds (such as acridones, acridines, other aza-aromatic polycycles and helicene-like structures) with potential applications. From some of the scaffolds obtained, biological evaluation in the frame of collaborations allowed properties of interest to be discovered (e.g., specific inhibition of protein kinases GSK-3 or PIM, related to cancer development).https://www.mdpi.com/2673-4583/12/1/20organic synthesismethodologyaromatic iodideheterocyclebiological activity |
| spellingShingle | Florence Mongin William Erb Frédéric Lassagne Aromatic Iodides: Synthesis and Conversion to Heterocycles Chemistry Proceedings organic synthesis methodology aromatic iodide heterocycle biological activity |
| title | Aromatic Iodides: Synthesis and Conversion to Heterocycles |
| title_full | Aromatic Iodides: Synthesis and Conversion to Heterocycles |
| title_fullStr | Aromatic Iodides: Synthesis and Conversion to Heterocycles |
| title_full_unstemmed | Aromatic Iodides: Synthesis and Conversion to Heterocycles |
| title_short | Aromatic Iodides: Synthesis and Conversion to Heterocycles |
| title_sort | aromatic iodides synthesis and conversion to heterocycles |
| topic | organic synthesis methodology aromatic iodide heterocycle biological activity |
| url | https://www.mdpi.com/2673-4583/12/1/20 |
| work_keys_str_mv | AT florencemongin aromaticiodidessynthesisandconversiontoheterocycles AT williamerb aromaticiodidessynthesisandconversiontoheterocycles AT fredericlassagne aromaticiodidessynthesisandconversiontoheterocycles |