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Recent Advances in Metal-Free Quinoline Synthesis

The quinoline ring system is one of the most ubiquitous heterocycles in the fields of medicinal and industrial chemistry, forming the scaffold for compounds of great significance. These include anti-inflammatory and antitumor agents, the antimalarial drugs quinine and chloroquine, and organic light-...

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Autores principales: Ramann, Ginelle A., Cowen, Bryan J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273574/
https://www.ncbi.nlm.nih.gov/pubmed/27483222
http://dx.doi.org/10.3390/molecules21080986
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author Ramann, Ginelle A.
Cowen, Bryan J.
author_facet Ramann, Ginelle A.
Cowen, Bryan J.
author_sort Ramann, Ginelle A.
collection PubMed
description The quinoline ring system is one of the most ubiquitous heterocycles in the fields of medicinal and industrial chemistry, forming the scaffold for compounds of great significance. These include anti-inflammatory and antitumor agents, the antimalarial drugs quinine and chloroquine, and organic light-emitting diodes. Quinolines were first synthesized in 1879, and since then a multitude of synthetic routes have been developed. Many of these methods, such as the Skraup, Doebner–Von Miller, and Friedlander quinoline syntheses, are well-known but suffer from inefficiency, harsh reaction conditions, and toxic reagents. This review focuses on recent transition metal-free processes toward these important heterocycles, including both novel routes and modifications to established methods. For example, variations on the Skraup method include microwave irradiation, ionic liquid media, and novel annulation partners, all of which have shown increased reaction efficiency and improved yield of the heteroring-unsubstituted quinoline products. Similarly, modifications to other synthetic routes have been implemented, with the quinoline products displaying a wide variety of substitution patterns.
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spelling pubmed-62735742018-12-28 Recent Advances in Metal-Free Quinoline Synthesis Ramann, Ginelle A. Cowen, Bryan J. Molecules Review The quinoline ring system is one of the most ubiquitous heterocycles in the fields of medicinal and industrial chemistry, forming the scaffold for compounds of great significance. These include anti-inflammatory and antitumor agents, the antimalarial drugs quinine and chloroquine, and organic light-emitting diodes. Quinolines were first synthesized in 1879, and since then a multitude of synthetic routes have been developed. Many of these methods, such as the Skraup, Doebner–Von Miller, and Friedlander quinoline syntheses, are well-known but suffer from inefficiency, harsh reaction conditions, and toxic reagents. This review focuses on recent transition metal-free processes toward these important heterocycles, including both novel routes and modifications to established methods. For example, variations on the Skraup method include microwave irradiation, ionic liquid media, and novel annulation partners, all of which have shown increased reaction efficiency and improved yield of the heteroring-unsubstituted quinoline products. Similarly, modifications to other synthetic routes have been implemented, with the quinoline products displaying a wide variety of substitution patterns. MDPI 2016-07-29 /pmc/articles/PMC6273574/ /pubmed/27483222 http://dx.doi.org/10.3390/molecules21080986 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Review
Ramann, Ginelle A.
Cowen, Bryan J.
Recent Advances in Metal-Free Quinoline Synthesis
title Recent Advances in Metal-Free Quinoline Synthesis
title_full Recent Advances in Metal-Free Quinoline Synthesis
title_fullStr Recent Advances in Metal-Free Quinoline Synthesis
title_full_unstemmed Recent Advances in Metal-Free Quinoline Synthesis
title_short Recent Advances in Metal-Free Quinoline Synthesis
title_sort recent advances in metal-free quinoline synthesis
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273574/
https://www.ncbi.nlm.nih.gov/pubmed/27483222
http://dx.doi.org/10.3390/molecules21080986
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