Advanced search
Start date
(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
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
[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

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