Diversely Substituted Quinolines via Rhodium-Catalyzed Alkyne Hydroacylation

Neuhaus, James D.; Morrow, Sarah M.; Brunavs, Michael; Willis, Michael C.

doi:10.1021/acs.orglett.6b00390

Cited by 49 publications

(16 citation statements)

References 52 publications

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“…This methodology has the advantage of high functional group tolerance thus allowing rapid synthesis of libraries of diversely substituted quinoline architectures. 85 Aerobic dehydrogenation of 1,2,3,4-tetrahydroquinolines (156), using heterogeneous cobalt oxide catalyst enabled an efficient route for the generation of corresponding quinolines (157) under mild conditions (Scheme 57). Application of Co 3 O 4 catalyst further aids in aerobic dehydrogenation process.…”

Section: Various Approaches For the Synthesis Of Quinolines And Theirmentioning

confidence: 99%

A review on transition-metal mediated synthesis of quinolines

2018

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Quinoline is one of the important class of heterocyclic compounds which have gained considerable importance because of its high pharmaceutical efficacy and broad range of biological activities such as anticancer, anti-malarial, anti-microbial and anti-asthmatic. As a consequence, the desire for new versatile and efficient route for the synthesis of quinoline scaffolds remains an active and growing area of interest both in academia and industry. However, developments of transition-metal catalyzed synthetic methods have witnessed a dominant position over the past few years for the synthesis of diverse range of complex heterocyclics containing quinoline scaffolds. This review specifically provides an overview of the literature available on the transitionmetal catalyzed synthetic methodologies for the synthesis of polysubstituted quinoline derivatives.

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Section: Various Approaches For the Synthesis Of Quinolines And Theirmentioning

confidence: 99%

A review on transition-metal mediated synthesis of quinolines

2018

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“…They are also considered at a clinical level and constitute the core structure of commercially available pharmaceuticals; nifedipine, nitrendipine and nimodipine are examples in this area. Moreover, this scaffold is also found in many natural products, [19] agrochemicals, [20] and dye‐sensitized solar cells [21] . In light of their wide use, several methodologies have been explored to generate this heterocycles.…”

Section: Introductionmentioning

confidence: 99%

Magnetically Retrievable Organocatalyst: An Emergent Green Method for The Rapid Formation of Biodynamically Significant Quinolines

Maurya

Sagir²,

Ansari

et al. 2021

ChemistrySelect

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Herein, highly efficient organocatalyst arginine coupled magnetic nanoparticles have been synthesized and aiming to catalyze synthesis of biodynamically significant quinolines. Results indicate that the catalyst is compatible with a wide range of functional groups and generates various quinoline derivatives in good to excellent yields under solvent free condition. Superior activity of the reported catalyst can be combine with the synergistic effect of the following factors: Firstly use of iron oxide nanoparticles as supports provide large surface areas, high surface‐to‐volume ratio, high reactivity and selectivity and lower consumption of energy, Secondly encapsulation of MNPs (Magnetic Nanoparticles) with L‐arginine not only prevent magnetic aggregation but also imparts many desirable properties like high thermal and chemical stability, finely disperse active sites and enhanced activity. Thirdly use of environmentally more benign, non‐toxic and much cheaper L‐arginine amino acid for coating agent need simple handling and storage. Fourthly potential recovery of this catalytic system by an external magnet, reduces waste, labour and cost, thus satisfy the requirements of green chemistry. Moreover such coating also provides sites for functionalization with other organic groups and thereby broaden their applicability in various research areas such as drug delivery, magnetic resonance imaging, biomedicine and especially in the field of heterocatalysis.

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“…Currently, to furnish wide structural and functional diversity of quinoline‐based compounds, classical approaches (such as Skraup, Doebner‐von Miller, Friedländer, Pfitzinger, Conrad‐Limpach, and Combes reactions) are used along with relevant new methods to assemble the quinoline core and introduce desirable substituents into the pre‐existing bicycle . In this context, we report a new synthesis of quinoline‐based structures by intramolecular reduction‐triggered transformations, of 4‐( o ‐nitroaryl)‐3‐acyl‐substituted 4,5‐dihydrofurans.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Functionalized Quinolines from 4‐(o‐Nitroaryl)‐Substituted 3‐Acyl‐4,5‐Dihydrofurans: Reductive Cyclization and C=C Bond Cleavage

et al. 2017

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A new synthetic approach to functionalized quinolines was developed based on the application of Zn–AcOH system as a simple and efficient reductive agent towards 4‐(o‐nitroaryl)‐3‐acyl‐substituted 4,5‐dihydrofurans. Reduction of 3‐carbonyl‐substituted dihydrofurans is accomplished by C=C double‐bond cleavage in the dihydrofuran ring and 1,6‐cyclization, which leads to 3,4‐dihydroquinolines. The latter can be easily oxidized to quinolines or reduced to tetrahydroquinolines. For dihydrofuran‐3‐carboxylates, reduction proceeds with retention of the dihydrofuran ring and affords a tricyclic dihydrofuroquinoline core under harsher conditions. The proposed general reaction pattern was supported by results of DFT calculations. Moreover, a similar reductive system can be successfully applied in the conversion of dihydrofuran acyclic precursors, γ‐(o‐nitroaryl) α,β‐unsaturated carbonyl compounds, into quinoline derivatives.

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Diversely Substituted Quinolines via Rhodium-Catalyzed Alkyne Hydroacylation

Cited by 49 publications

References 52 publications

A review on transition-metal mediated synthesis of quinolines

A review on transition-metal mediated synthesis of quinolines

Magnetically Retrievable Organocatalyst: An Emergent Green Method for The Rapid Formation of Biodynamically Significant Quinolines

Synthesis of Functionalized Quinolines from 4‐(o‐Nitroaryl)‐Substituted 3‐Acyl‐4,5‐Dihydrofurans: Reductive Cyclization and C=C Bond Cleavage

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