o-Benzenedisulfonimide as a reusable Brønsted acid catalyst for an efficient and facile synthesis of quinolines via Friedländer annulation

Barbero, Margherita; Bazzi, Stefano; Cadamuro, Silvano; Dughera, Stefano

doi:10.1016/j.tetlet.2010.02.139

Cited by 36 publications

(18 citation statements)

References 39 publications

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“…One example was reported by Dughera and coworkers [32], who had previously utilized the acid catalyst o-benzenedisulfonimide (34, Figure 16) in several syntheses and found it to be non-corrosive, non-volatile, and recyclable. They applied this acid catalyst to a solvent-free Friedländer reaction of 2-aminoarylketones (32) with various carbonyl compounds (33).…”

Section: Friedländer Reactionmentioning

confidence: 97%

Recent Advances in Metal-Free Quinoline Synthesis

2016

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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.

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Section: Friedländer Reactionmentioning

confidence: 97%

Recent Advances in Metal-Free Quinoline Synthesis

2016

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“…In 2010, Dughera and co‐workers utilized the non‐corrosive, non‐volatile, and recyclable o ‐benzenedisulfonimide acid catalyst to a solvent‐free Friedländer reaction (Scheme ). In this method, they obtained several 2,3‐disubstituted quinolines, including fused five‐member rings, with good to excellent yields via 2‐aminoarylketones with various carbonyl compounds.…”

Section: Synthesis Routes To Functionalized Quinolinesmentioning

confidence: 99%

“…In this process, the first step yields 2,4-substituted tetrahydroquinoline convertedt o2 -phenyl substituted quinolines under vacuum distillation with tosylic acid (p-TsOH) (Scheme 3). [18] In 2010, Dughera and co-workers [19] utilized the non-corrosive, non-volatile, and recyclable o-benzenedisulfonimidea cid catalystt oasolvent-free Friedländer reaction (Scheme 4). In this method, they obtained several2 ,3-disubstituted quinolines, including fused five-memberr ings, with good to excellent yields via 2-aminoarylketones with various carbonyl compounds.…”

Section: Anilinederived Synthesesmentioning

confidence: 99%

Organocatalyzed Synthesis of Functionalized Quinolines

Niu

Liang

2019

Chemistry An Asian Journal

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As one of the most widely investigated compound skeleton, quinolines possess important medicinal and biological activities. As such, ag reat number of literatures, including reviews, have reported various methodologies to construct quinolines. Recently,o rganocatalyzed reactions have attracted the attention of organic chemists due to its being "green" because the reactions avoid the use of toxic metals.I nt his review, various distinctive contributionsa re surveyed with specific emphasis on organocatalyzed reactions for quinoline core constructions.

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“…Generally, the reactive α-methylene group is part of unsymmetrical ketones, 8 1,3-dicarbonyl compounds 9 or β-ketoesters. [10][11][12] Quinolines from these precursors present a 3-acyl group such as acetyl, benzoyl, thienyl, furyl, carboxylate and trifluoroacetyl. 9 However, quinolines with electron-withdrawing groups such as perfluoroalkyl, trichloromethyl and dichloromethyl groups attached at 3-position cannot be obtained from unsymmetrical ketones, 8 1,3-dicarbonyl compounds 9 or β-ketoesters due to the difficulty to obtain the precursors.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel quinolines using TsOH/ionic liquid under microwave

Prola

Buriol

Frizzo

et al. 2012

J. Braz. Chem. Soc.

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Neste trabalho, 3-haloacetil-4-metilquinolinas foram sintetizadas a partir da reação de 4-alcóxi-3-alquen-2-onas [R In this work, 3-haloacetyl-4-methylquinolines were synthesized from the reaction of 4-alkoxy-3-alken-2-ones [R 1 C(O)CH=C(R 2 )OCH 3 , where R 1 = CF 3 , CCl 3 , CHCl 2 , CF 2 Cl, CF 2 CF 3 and R 2 = Me, Et, Pr, Bu, i-Bu and i-Pe] and 2-aminoacetophenone. The reaction was performed in ionic liquid and 4-toluene sulfonic acid under microwave irradiation. Results showed that the catalytic method was effective. Products were formed in a short time (10-20 min) and presented good yields (70-91%).

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o-Benzenedisulfonimide as a reusable Brønsted acid catalyst for an efficient and facile synthesis of quinolines via Friedländer annulation

Cited by 36 publications

References 39 publications

Recent Advances in Metal-Free Quinoline Synthesis

Recent Advances in Metal-Free Quinoline Synthesis

Organocatalyzed Synthesis of Functionalized Quinolines

Synthesis of novel quinolines using TsOH/ionic liquid under microwave

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