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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Bibliographic Details
Published in:Journal of organic chemistry 2021-10, Vol.86 (19), p.13402-13419
Main Authors: 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
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01521