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Synthesis of 7‑Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents
We have prepared a library of functionalized quinolines through the magnesiation of 7-chloroquinolines under mild conditions, employing both batch and continuous flow conditions. The preparation involved the generation of mixed lithium-magnesium intermediates, which were reacted with different elect...
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| Published in: | Journal of organic chemistry 2021-10, Vol.86 (19), p.13402-13419 |
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| Main Authors: | , , , , , , , , , , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-a351t-36ad59f5f6fd17d95443ab9a6d97e30e1fd78b7d6ee7b11a938ed4b1d5bec2773 |
| container_end_page | 13419 |
| container_issue | 19 |
| container_start_page | 13402 |
| container_title | Journal of organic chemistry |
| container_volume | 86 |
| creator | Murie, Valter E Nicolino, Paula V dos Santos, Thiago Gambacorta, Guido Nishimura, Rodolfo H. V Perovani, Icaro S Furtado, Luciana C Costa-Lotufo, Leticia V Moraes de Oliveira, Anderson Vessecchi, Ricardo Baxendale, Ian R Clososki, Giuliano C |
| description | We have prepared a library of functionalized quinolines through the magnesiation of 7-chloroquinolines under mild conditions, employing both batch and continuous flow conditions. The preparation involved the generation of mixed lithium-magnesium intermediates, which were reacted with different electrophiles. Mixed lithium-zinc reagents allowed the synthesis of halogenated and arylated derivatives. Some of the synthesized 4-carbinol quinolines have shown interesting antiproliferative properties, their hydroxyl group being a suitable amino group bioisostere. We also report a two-step approach for optically active derivatives. |
| doi_str_mv | 10.1021/acs.joc.1c01521 |
| format | article |
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| ispartof | Journal of organic chemistry, 2021-10, Vol.86 (19), p.13402-13419 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| title | Synthesis of 7‑Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents |
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