Advanced search
Start date
Betweenand
(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

Full text
Author(s):
Show less -
Murie, Valter E. [1] ; Nicolino, V, Paula ; dos Santos, Thiago [2] ; Gambacorta, Guido [3] ; Nishimura, V, Rodolfo H. ; Perovani, Icaro S. [4] ; Furtado, Luciana C. [5] ; Costa-Lotufo, V, Leticia ; de Oliveira, Anderson Moraes [4] ; Vessecchi, Ricardo [4] ; Baxendale, Ian R. [3] ; Clososki, Giuliano C. [4, 3]
Total Authors: 12
Affiliation:
[1] V, Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, Dept Ciencias BioMol, BR-14040903 Ribeirao Preto - Brazil
[2] Nicolino, Paula, V, V, Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, Dept Ciencias BioMol, BR-14040903 Ribeirao Preto - Brazil
[3] Univ Durham, Dept Chem, Durham DH1 3LE - England
[4] Univ Sao Paulo, Fac Filosofia Ciencias & Letras Ribeirao Preto, Dept Quim, BR-14040901 Ribeirao Preto - Brazil
[5] V, Univ Sao Paulo, Inst Ciencias Biomed, Dept Farmacol, BR-05508900 Sao Paulo - Brazil
Total Affiliations: 5
Document type: Journal article
Source: Journal of Organic Chemistry; v. 86, n. 19, p. 13402-13419, OCT 1 2021.
Web of Science Citations: 0
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. (AU)

FAPESP's process: 13/00758-0 - Application of organometallic reagents in the synthesis of new quinoline derivatives with potential antimalarial activity
Grantee:Paula Valim Nicolino
Support type: Scholarships in Brazil - Master
FAPESP's process: 15/21364-6 - Applicantion of Organometallic Reagents in the Directed Functionalization of Quinolines Aimming the Synthesis of Medicinal Interest Compounds
Grantee:Valter Eduardo Murie
Support type: Scholarships in Brazil - Doctorate
FAPESP's process: 19/05838-9 - Flow modified Lehmstedt-Tanasescu reactions for the scaled production of medicinally important heterocyclic building blocks
Grantee:Valter Eduardo Murie
Support type: Scholarships abroad - Research Internship - Doctorate
FAPESP's process: 18/14150-8 - Selective aromatic functionalization: Methodological Studies and new applications in the synthesis of BIOATIVE compounds
Grantee:Giuliano Cesar Clososki
Support type: Regular Research Grants
FAPESP's process: 15/17177-6 - Integrative approach on the sustainable prospection of marine natural products: from diversity to anticancer compounds
Grantee:Leticia Veras Costa Lotufo
Support type: BIOTA-FAPESP Program - Thematic Grants