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Keywords = Skraup reaction

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14 pages, 2102 KiB  
Article
Glycerol and Q-Tubes: Green Catalyst and Technique for Synthesis of Polyfunctionally Substituted Heteroaromatics and Anilines
by Douaa Salman AlMarzouq and Noha M. Hilmy Elnagdi
Molecules 2019, 24(9), 1806; https://doi.org/10.3390/molecules24091806 - 10 May 2019
Cited by 12 | Viewed by 4791
Abstract
The role of glycerol as a green bio-based solvent, reactant, and/or a catalyst in the synthesis of novel heterocycles, under pressure, is studied. Synthesis of novel quinolines in good yields using a new modified Skraup synthesis, utilizing glycerol and pressure Q-tubes, is demonstrated. [...] Read more.
The role of glycerol as a green bio-based solvent, reactant, and/or a catalyst in the synthesis of novel heterocycles, under pressure, is studied. Synthesis of novel quinolines in good yields using a new modified Skraup synthesis, utilizing glycerol and pressure Q-tubes, is demonstrated. Novel aniline trimers are prepared using glycerol, and substituted anilines under pressure, in acidic medium and water. Glycerol was employed as a catalyst and a green solvent in the synthesis of novel pyridazines 13a–c. The mechanisms of the reactions and the catalytic effect of glycerol in protic and aprotic media are fully discussed. The structures of the synthesized compounds were determined via X-ray crystallography and spectroscopic methods. Full article
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23 pages, 12785 KiB  
Review
Recent Advances in Metal-Free Quinoline Synthesis
by Ginelle A. Ramann and Bryan J. Cowen
Molecules 2016, 21(8), 986; https://doi.org/10.3390/molecules21080986 - 29 Jul 2016
Cited by 145 | Viewed by 25114
Abstract
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. [...] Read more.
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. Full article
(This article belongs to the Collection Heterocyclic Compounds)
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9 pages, 102 KiB  
Article
Synthesis and Fluorescence Properties of 5,7-Diphenylquinoline and 2,5,7-Triphenylquinoline Derived from m-Terphenylamine
by Shujian Qi, Kehui Shi, Hongyin Gao, Qiancai Liu and Hong Wang
Molecules 2007, 12(5), 988-996; https://doi.org/10.3390/12050988 - 12 May 2007
Cited by 19 | Viewed by 10488
Abstract
Synthesis of 5,7-phenylquinoline from the Skraup reaction of m-terphenyl-amine and glycerol in the presence of acid is reported. Further reaction of 5,7-diphenyl-quinoline with phenyl lithium prepared in situ led to the formation of 2,5,7-triphenyl-quinoline. All of the products and their intermediates were characterized [...] Read more.
Synthesis of 5,7-phenylquinoline from the Skraup reaction of m-terphenyl-amine and glycerol in the presence of acid is reported. Further reaction of 5,7-diphenyl-quinoline with phenyl lithium prepared in situ led to the formation of 2,5,7-triphenyl-quinoline. All of the products and their intermediates were characterized and the UV-Vis and photo-luminescence (PL) spectra of m-terphenylamine, 5,7-diphenylquinoline and 2,5,7-triphenylquinoline are also reported. Full article
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