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Synthesis of 7-Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents

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.

Synthesis of 7-Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents Thumbnail


Authors

Valter E. Murie

Paula V. Nicolino

Thiago dos Santos

Guido Gambacorta

Rodolfo H.V. Nishimura

Icaro S. Perovani

Luciana C. Furtado

Leticia V. Costa-Lotufo

Anderson Moraes de Oliveira

Ricardo Vessecchi

Giuliano C. Clososki



Abstract

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.

Journal Article Type Article
Online Publication Date Sep 23, 2021
Publication Date Oct 1, 2021
Deposit Date Jan 6, 2022
Publicly Available Date Sep 23, 2022
Journal The Journal of Organic Chemistry
Print ISSN 0022-3263
Electronic ISSN 1520-6904
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 86
Issue 19
Pages 13402-13419
DOI https://doi.org/10.1021/acs.joc.1c01521
Public URL https://durham-repository.worktribe.com/output/1219398

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Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.1c01521





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