RECENT ADVANCES IN SELECTIVE FUNCTIONALIZATION OF QUINOLINES

Author(s)

Dartagnan S. P. Ferreira ^[1] ; Valter E. Murie ^[2] ; Thiago dos Santos ^[3] ; Paulo C. Vieira ^[4] ; Giuliano C. Clososki ^[5]

Affiliation

^[1] Universidade de São Paulo. Departamento de Ciências Biomoleculares. Faculdade de Ciências Farmacêuticas de Ribeirão Preto - Brasil

^[2] Universidade de São Paulo. Departamento de Ciências Biomoleculares. Faculdade de Ciências Farmacêuticas de Ribeirão Preto - Brasil

^[3] Universidade de São Paulo. Departamento de Ciências Biomoleculares. Faculdade de Ciências Farmacêuticas de Ribeirão Preto - Brasil

^[4] Universidade de São Paulo. Departamento de Ciências Biomoleculares. Faculdade de Ciências Farmacêuticas de Ribeirão Preto - Brasil

^[5] Universidade de São Paulo. Departamento de Ciências Biomoleculares. Faculdade de Ciências Farmacêuticas de Ribeirão Preto - Brasil

• Document type: Journal article
• Source: Química Nova; v. 44, n. 5, p. 599-615, 2021-07-26.

Abstract

Heterocyclic compounds form an important and extensive group of organic substances. Among nitrogenous heterocyclic molecules, quinolines stand out for exhibiting attractive chemical and biological properties. These substances can be used as ligands, sensors, luminescent and agrochemical materials. In addition, quinoline-containing compounds can exhibit a wide spectrum of pharmacological properties, allowing their use in several approved drugs nowadays. Due to its importance, the synthesis of molecules containing this nucleus becomes a point of interest for synthetic chemists. In this way, several methodologies have been recently developed to prepare quinoline derivatives with high structural diversity. Such chemical transformations allow the chemical modification of these rings with high selectivity and tolerance to diverse functional groups and these properties have been conveniently used in the preparation of biologically active molecules containing this unit. Herein, we present a review of the main methodologies employed in the selective functionalization of quinolines in the last twenty years. In this context, a brief introduction addressing general synthetic and medicinal aspects related to the functionalization positions of the quinoline ring is presented. Several methodologies used in the functionalization of this moiety are discussed, as well relevant synthetic applications, both in the preparation and functionalization of substances of biological interest. (AU)

• 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 Opportunities: 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 Opportunities: Regular Research Grants
• 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 Opportunities: Scholarships in Brazil - Doctorate