One-pot synthesis of quinoline-4-carboxylic acid derivatives in water: Ytterbium perfluorooctanoate catalyzed Doebner reaction

Wang, Limin; Hu, Liang; Chen, Hong-Juan; Sui, Yuan‐Yuan; Shen, Wei

doi:10.1016/j.jfluchem.2009.01.002

Cited by 41 publications

(13 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Wang et al developed a method for the synthesis of 2-phenylquinoline-4-carboxylic acids, 10 by the treatment of pyruvic acid with substituted aniline and benzaldehyde in the presence of rare-earth metal catalysts in water under reflux condition [11]. Kouznetsov Two molecules of o-haloacetophenones condensed with urea or primary amines yielded certain halogen-substituted quinolones, 13.…”

Section: Synthesismentioning

confidence: 99%

Quinoline Heterocycles: Synthesis and Bioactivity

Rajesh¹

2020

Heterocycles - Synthesis and Biological Activities

View full text Add to dashboard Cite

Among heterocyclic compounds, quinoline is a privileged scaffold that appears as an important construction motif for the development of new drugs. Quinoline nucleus is endowed with a variety of therapeutic activities, and new quinolone derivatives are known to be biologically active compounds possessing several pharmacological activities. Many new therapeutic agents have been developed by using quinoline nucleus. Hence, quinoline and its derivatives form an important class of heterocyclic compounds for the new drug development. Numerous synthetic routes have been developed for the synthesis of quinoline and its derivatives due to its wide range of biological and pharmacological activities. The article covers the synthesis as well as biological activities of quinoline derivatives such as antimalarial, anticancer, antibacterial, anthelmintic, antiviral, antifungal, antiinflammatory, analgesic, cardiovascular, central nervous system, hypoglycemic, and miscellaneous activities.

show abstract

Section: Synthesismentioning

confidence: 99%

Quinoline Heterocycles: Synthesis and Bioactivity

Rajesh¹

2020

Heterocycles - Synthesis and Biological Activities

View full text Add to dashboard Cite

show abstract

“…The general procedure, combining aniline with benzaldehyde and pyruvic acid to form 2-substituted quinoline-4-carboxylic acids, typically suffers from low yields or long reaction times. Even previous examples of modified procedures require the use of harsh reaction conditions, large amounts of organic solvent, or special apparatus [14].…”

Section: Doebner Reactionmentioning

confidence: 99%

Recent Advances in Metal-Free Quinoline Synthesis

2016

View full text Add to dashboard Cite

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. 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.

show abstract

“…Several methods have been reported for the synthesis of quinolines, such as Dobner 7 , Skraup 8 , Pfitzinger and Friedlander 9,10 . But, among them, Friedlander reaction is the most simple and straightforward method.…”

Section: Introductionmentioning

confidence: 99%

Silica-based sulfonic acid (MCM-41-SO3H): a practical and efficient catalyst for the synthesis of highly substituted quinolines under solvent-free conditions at ambient temperature

Maleki¹,

Javanshir²,

Sharifi³

2014

10.5267/j.ccl

View full text Add to dashboard Cite

In this work, a variety of highly substituted quinolines were readily synthesized via Friedlander annulation using Brönsted acid silica-based sulfonic acid as a modified catalyst under solventfree conditions at room temperature. This efficient procedure has the advantages of giving the target compounds in high yields, short reaction times, simple workup procedure, reusability of the catalyst, and environmentally benign conditions.

show abstract

One-pot synthesis of quinoline-4-carboxylic acid derivatives in water: Ytterbium perfluorooctanoate catalyzed Doebner reaction

Cited by 41 publications

References 45 publications

Quinoline Heterocycles: Synthesis and Bioactivity

Quinoline Heterocycles: Synthesis and Bioactivity

Recent Advances in Metal-Free Quinoline Synthesis

Silica-based sulfonic acid (MCM-41-SO3H): a practical and efficient catalyst for the synthesis of highly substituted quinolines under solvent-free conditions at ambient temperature

Contact Info

Product

Resources

About