The Tautomeric Persistence of Electronically and Sterically Biased 2‐Quinolinones

Volle, J.‐N.; Mävers, Ursula; Schlosser, Manfred

doi:10.1002/ejoc.200800123

Cited by 13 publications

(3 citation statements)

References 83 publications

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“…However, for 3‐pyridones and 22 , the lactim form is favored over the lactam form. In the latter case, electronic effects explain this observation and have already been described elsewhere 16b,16f. Thus, a different reaction pathway occurs in which the formation of the phosphite is simply the result of a protolysis reaction of cation 1 3+ (Scheme ).…”

Section: Resultssupporting

confidence: 60%

Facile Fabrication of Nanoparticles Confined in Graphene Films and Their Electrochemical Properties

Chen

Zhu

Qiu

et al. 2013

Chemistry A European J

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The development of novel nanostructured electrode materials with high performance and based on abundant elements is a key element in the societal pursuit of sustainable energy. Graphene-based structures with rich macroporosity and high conductive networks are promising components to develop novel electrode materials. Herein, we described a facile procedure to confine Ni(OH)2 particles in a graphene film, leading to a new sandwich-like hybrid structure. The hybrid film offers simultaneously ordered ion diffusion channels and high electrical conductivity, which facilitate the improvement of both electrode kinetics and electrochemical stability, thus leading to high capacitance, fast rate capability, and stable cycle life as supercapacitor materials. This work provides a facile pathway for optimized structures for electrode materials, and represents a benefit for the global issues of energy shortage and environmental pollution.

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Section: Resultssupporting

confidence: 60%

Facile Fabrication of Nanoparticles Confined in Graphene Films and Their Electrochemical Properties

Chen

Zhu

Qiu

et al. 2013

Chemistry A European J

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“…The relative thermodynamic stabilities of the quinolone and quinoline forms are predicted to be similar 25, 26, 27. The more polar quinolone tautomer is predicted to be predominantly adopted in the solid state and in aqueous solution 25, 26, 28. The presence of a carboxylate group at the 3 position could act as a hydrogen bond acceptor for the 4-OH group and thus might stabilize the enol quinoline tautomer 25.…”

Section: Synthesis Of Targeted Analogues Of 7 Andmentioning

confidence: 99%

Synthesis and structure–activity relationships of antimalarial 4-oxo-3-carboxyl quinolones

Zhang

Guiguemde

Sigal

et al. 2010

Bioorganic & Medicinal Chemistry

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Malaria is endemic in tropical and subtropical regions of Africa, Asia, and the Americas. The increasing prevalence of multi-drug-resistant Plasmodium falciparum drives the ongoing need for the development of new antimalarial drugs. In this light, novel scaffolds to which the parasite has not been exposed are of particular interest. Recently, workers at the Swiss Tropical Institute discovered two novel 4-oxo-3-carboxyl quinolones active against the intra-erythrocytic stages of P. falciparum while carrying out rationally directed low-throughput screening of potential antimalarial agents as part of an effort directed by the World Health Organization. Here we report the design, synthesis, and preliminary pharmacologic characterization of a series of analogues of 4-oxo-3-carboxyl quinolones. These studies indicate that the series has good potential for preclinical development.

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“…The dominant presence of 2-quinolones over 2-hydroxyquinoline in nonaqueous phase or in solid state has been explained by the hydrogen-bonded dimeric stabilization of 2-quinolones [ 65 ]. In addition to hydrogen bonding, the equilibrium between the two forms appears to be determined by factors such as solvent polarity [ 66 ], steric hindrance, and the electronic properties of substituents [ 67 ]. Studies on the equilibrium of six-membered N -heterocycles indicates that the reduced aromaticity may contribute to the tautomerization of 2-quinolones as well [ 68 ].…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in One-Pot Modular Synthesis of 2-Quinolones

2020

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It is known that 2-quinolones are broadly applicable chemical structures in medicinal and agrochemical research as well as various functional materials. A number of current publications about their synthesis and their applications emphasize the importance of these small molecules. The early synthetic chemistry originated from the same principle of the classical Friedländer and Knorr procedures for the preparation of quinolines. The analogous processes were developed by applying new synthetic tools such as novel catalysts, the microwave irradiation method, etc., whereas recent innovations in new bond forming reactions have allowed for novel strategies to construct the core structures of 2-quinolones beyond the bond disconnections based on two classical reactions. Over the last few decades, some reviews on structure-based, catalyst-based, and bioactivity-based studies have been released. In this focused review, we extensively surveyed recent examples of one-pot reactions, particularly in view of modular approaches. Thus, the contents are categorized as three major sections (two-, three-, and four-component reactions) according to the number of reagents that ultimately compose atoms of the core structures of 2-quinolones. The collected synthetic methods are discussed from the perspectives of strategy, efficiency, selectivity, and reaction mechanism.

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The Tautomeric Persistence of Electronically and Sterically Biased 2‐Quinolinones

Cited by 13 publications

References 83 publications

Facile Fabrication of Nanoparticles Confined in Graphene Films and Their Electrochemical Properties

Facile Fabrication of Nanoparticles Confined in Graphene Films and Their Electrochemical Properties

Synthesis and structure–activity relationships of antimalarial 4-oxo-3-carboxyl quinolones

Recent Advances in One-Pot Modular Synthesis of 2-Quinolones

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