The Chemistry of 4-Hydroxyquinolines.

Reitsema, Robert H.

doi:10.1021/cr60134a002

Cited by 140 publications

(35 citation statements)

References 81 publications

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“…Various synthetic routes towards 4‐quinolones have been developed8 and approaches based on cyclocondensation, such as the Niementowski,9 Conrad–Limpach10 and Camps cyclizations,11 are widely employed. The major shortcoming in these methods is the required harsh reaction conditions, which rely on the use of high temperatures and/or strong bases that dramatically limit the scope of these reactions.…”

Section: Introductionmentioning

confidence: 99%

On the Nature of Interactions between Ionic Liquids and Small Amino‐Acid‐Based Biomolecules

et al. 2013

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During the last decade, ionic liquids (ILs) have revealed promising properties and applications in many research fields, including biotechnology and biological sciences. The focus of this contribution is to give a critical review of the phenomena observed and current knowledge of the interactions occurring on a molecular basis. As opposed to the huge advances made in understanding the properties of proteins in ILs, complementary investigations dealing with interactions between ILs and peptides or oligopeptides are underrepresented and are mostly only of phenomenological nature. However, the field has received more attention in the last few years. This Review features a meta-analysis of the available data and findings and should, therefore, provide a basis for a scientifically profound understanding of the nature and mechanisms of interactions between ILs and structured or nonstructured peptides. Fundamental aspects of the interactions between different peptides/oligopeptides and ILs are complemented by sections on the experimental (spectroscopy, structural biology) and theoretical (computational chemistry) possibilities to explain the phenomena reported so far in the literature. In effect, this should lead to the development of novel applications and support the understanding of IL-solute interactions in general.

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Section: Introductionmentioning

confidence: 99%

On the Nature of Interactions between Ionic Liquids and Small Amino‐Acid‐Based Biomolecules

et al. 2013

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“…Although this is considered a universal process [20], it presents several challenges. The original solvent-free method was relatively inefficient, however the high-energy imine-enol intermediate compulsory for cyclization necessitated any solvent added to the mixture to be high-boiling.…”

Section: Conrad-limpach Reactionmentioning

confidence: 99%

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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“…Although different methods have been described in the literature, efficient, large-scale, cheap technologies are still needed. Current strategies for the synthesis of quinoline derivatives include cyclization reactions starting from benzene (or cyclohexane) derivatives with N-functionalities, but these compounds have also been prepared by various conventionally named reactions, such as Skraup, 4 Friedländer, 5 Doebner-von Miller, 6 Pfitzinger, 7 Conrad-Limpach, 8 and Combes. 9 Unfortunately, these methods for quinoline synthesis often do not allow for adequate diversity and substitution on the quinoline ring system.…”

Section: Introductionmentioning

confidence: 99%

Simple and convenient preparation of novel 6,8-disubstituted quinoline derivatives and their promising anticancer activities

Ökten¹,

Çakmak²,

Erenler³

et al. 2013

Turk J Chem

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A short and easy route is described for 6,8-disubstituted derivatives of quinoline and 1,2,3,4-tetrahydroquinoline from 6,8-dibromoquinolines 2 and 7 by various substitution reactions. While copper-promoted substitution of 6,8-dibromide 2 produced monomethoxides 3 and 4, a prolonged reaction time mainly afforded dimethoxide 6 instead of 5, whose aromatization with DDQ and substitution reaction of dibromide 7 with NaOMe in the presence of CuI also gave rise to dimethoxide 6. Several 6,8-disubstituted quinolines were obtained by treatment of 6,8-dibromoquinoline (7) with n -BuLi followed by trapping with an electrophile [Si(Me) 3 Cl, S 2 (Me) 2, and DMF]. Furthermore, 7 was also converted to mono and dicyano derivatives. The anticancer activities of compounds 2, 7, 6, 12, 13, 15, and 16 against HeLa, HT29, and C6 tumor cell lines were tested, and 6,8-dibromo-1,2,3,4-tetrahydroquinoline (2) and 6,8-dimethoxyquinoline (6) showed significant anticancer activities against the tumor cell lines.

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The Chemistry of 4-Hydroxyquinolines.

Cited by 140 publications

References 81 publications

On the Nature of Interactions between Ionic Liquids and Small Amino‐Acid‐Based Biomolecules

On the Nature of Interactions between Ionic Liquids and Small Amino‐Acid‐Based Biomolecules

Recent Advances in Metal-Free Quinoline Synthesis

Simple and convenient preparation of novel 6,8-disubstituted quinoline derivatives and their promising anticancer activities

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