Efficient Metal‐Free Synthesis of Various Pyrido[2′,1′:2,3]imidazo‐ [4,5‐<i>b</i>]quinolines

Arnould, Mathieu; Hiebel, Marie‐Aude; Massip, Stéphane; Léger, J. M.; Jarry, Christian; Berteina‐Raboin, Sabine; Guillaumet, Gérald

doi:10.1002/chem.201300961

Cited by 32 publications

(17 citation statements)

References 72 publications

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“…In 2013, Berteina‐Raboin and Guillaumet reported DBU catalyzed intramolecular synthesis of quinolines as well, they picked up (ethynyl)H‐imidazo[1,2‐a]pyridin‐3‐amines as reactants. DBU prompts deprotonation and hydroarylation of the triple bond in the reaction, the next aromatization leads to the final products (Scheme ).…”

Section: Synthesis Routes To Functionalized Quinolinesmentioning

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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Section: Synthesis Routes To Functionalized Quinolinesmentioning

confidence: 99%

Organocatalyzed Synthesis of Functionalized Quinolines

Niu

Liang

2019

Chemistry An Asian Journal

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“…The activation of aryl halides with copper dates back to 1901, in a classical reaction called the Ullmann reaction [27]. Considering the valuable reports on the association of GBB-adducts with post-transformations affording a unique diversification strategy for the synthesis of novel compounds [28][29][30][31][32][33], herein we report a new coupled GBB-MCR-Ullmann-type N -arylation affording fused pentacyclic heterocycles. …”

Section: Introductionmentioning

confidence: 98%

Combined isocyanide-based multi-component Ullmann-type reaction: an efficient access to novel nitrogen-containing pentacyclic compounds

et al. 2015

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2-Chloro-3-formyl quinoline has been applied as an aldehyde moiety in the Groebke-Blackburn-Bienaymé multi-component reaction with isocyanides, 2-aminoazines, and 2-aminoazole to afford the desired adducts which are amenable for further cyclization on the basis of Ullmann-type coupling. The copper iodide-mediated intramolecular C-N bond formation in the second step gave an easy access to a series of imidazo[4[Formula: see text],5[Formula: see text]:4,5]pyrrolo[2,3-b]quinoline derivatives in moderate to good yields.

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“…The GBB reaction can be catalyzed by simple Brønsted acids, such as HClO 4 , [18][19][20] p-toluenesulfonic acid (PTSA), 21 AcOH, 22 HCl, 23,24 as well as SiO 2 /H 2 SO 4 . 25 Also, GBB reactions catalyzed by heterogeneous catalysts such as succinyl-β-cyclodextrin, 26 calix [6]arene-SO 3 H surfactant, 27 multi-walled carbon nanotubes/H 2 SO 4 , 28 cellulose@Fe 2 O 3 nanoparticles (NPs), 29 and fluconazole modified silicacoated magnetite NPs (Fe 3 O 4 @SiO 2 -Flu) 30 were recently described.…”

Section: Introductionmentioning

confidence: 99%

A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating

Santos

Anjos

Gibeli

et al. 2020

J. Braz. Chem. Soc.

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Over the last twenty years, the Groebke-Blackburn-Bienaymé (GBB) reaction has been emerged as a powerful tool to access different nitrogen-based heterocycles as privileged scaffolds in medicinal chemistry. This multicomponent reaction is usually catalyzed by ordinary Brønsted or Lewis acid catalysts. Herein, we present a comparative study on the catalytic efficiencies of different rare earth triflates in GBB reactions under microwave heating, involving 2-aminopyridine or 2-aminothiazole, as aminoazole component, and different aldehydes and aliphatic isocyanides. The use of gadolinium(III) triflate as cheaper alternative catalyst for the most commonly used scandium(III) triflate was acknowledged for the first time, and a library of twenty three imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles could be obtained in good to excellent yields.

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Efficient Metal‐Free Synthesis of Various Pyrido[2′,1′:2,3]imidazo‐ [4,5‐b]quinolines

Cited by 32 publications

References 72 publications

Organocatalyzed Synthesis of Functionalized Quinolines

Organocatalyzed Synthesis of Functionalized Quinolines

Combined isocyanide-based multi-component Ullmann-type reaction: an efficient access to novel nitrogen-containing pentacyclic compounds

A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating

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