Ionic liquid-mediated synthesis and functionalization of heterocyclic compounds

Abonı́a, Rodrigo; Laali, Kenneth K.

doi:10.1016/bs.aihch.2018.12.002

Cited by 9 publications

(5 citation statements)

References 302 publications

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“…Also, a good number of quinazoline derivatives are currently in different stages of clinical practice, and some have been sold as drugs. Based on bicyclic imidazolium-and triazolium-based ILs in combination with microwave-assisted organic synthesis, we successfully synthesized tryptanthrin, batracylin, and rutaecarpine using the rapid, one-pot, and high-yielding method and investigated their biological activities when appropriate [13][14][15].…”

Section: Ionic Liquids Are Designable and Structurally Tunable 21 Ion...mentioning

confidence: 99%

Expeditious Discovery of Small-Molecule Thermoresponsive Ionic Liquid Materials: A Review

Li,

Chu

2023

Molecules

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Ionic liquids (ILs) are a class of low-melting molten salts (<100 °C) constituted entirely of ions, and their research has gained tremendous attention in line with their remarkably growing applications (>124,000 publications dated 30 August 2023 from the Web of ScienceTM). In this review, we first briefly discussed the recent developments and unique characteristics of ILs and zwitterionic liquids (ZILs). Compared to molecular solvents and other conventional organic compounds, (zwitter) ionic liquids carry negligible volatility and are potentially recyclable and reusable. For structures, both ILs and ZILs can be systematically tailor-designed and engineered and are synthetically fine-tunable. As such, ionic liquids, including chiral, supported, task-specific ILs, have been widely used as powerful ionic solvents as well as valuable additives and catalysts for many chemical reactions. Moreover, ILs have demonstrated their value for use as polymerase chain reaction (PCR) enhancers for DNA amplification, chemoselective artificial olfaction for targeted VOC analysis, and recognition-based affinity extraction. As the major focus of this review, we extensively discussed that small-molecule thermoresponsive ILs (TILs) and ZILs (zwitterionic TILs) are new types of smart materials and can be expeditiously discovered through the structure and phase separation (SPS) relationship study by the combinatorial approach. Using this SPS platform developed in our laboratory, we first depicted the rapid discovery of N,N-dialkylcycloammonium and 1,3,4-trialkyl-1,2,3-triazolium TILs that concomitantly exhibited LCST (lower critical solution temperature) phase transition in water and displayed biochemically attractive Tc values. Both smart IL materials were suited for applications to proteins and other biomolecules. Zwitterionic TILs are ZILs whose cations and anions are tethered together covalently and are thermoresponsive to temperature changes. These zwitterionic TIL materials can serve as excellent extraction solvents, through temperature change, for biomolecules such as proteins since they differ from the common TIL problems often associated with unwanted ion exchanges during extractions. These unique structural characteristics of zwitterionic TIL materials greatly reduce and may avoid the denaturation of proteins under physiological conditions. Lastly, we argued that both rational structural design and combinatorial library synthesis of small-molecule TIL materials should take into consideration the important issues of their cytotoxicity and biosafety to the ecosystem, potentially causing harm to the environment and directly endangering human health. Finally, we would concur that before precise prediction and quantitative simulation of TIL structures can be realized, combinatorial chemistry may be the most convenient and effective technology platform to discover TIL expeditiously. Through our rational TIL design and combinatorial library synthesis and screening, we have demonstrated its power to discover novel chemical structures of both TILs and zwitterionic TILs. Undoubtedly, we will continue developing new small-molecule TIL structures and studying their applications related to other thermoresponsive materials.

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Section: Ionic Liquids Are Designable and Structurally Tunable 21 Ion...mentioning

confidence: 99%

Expeditious Discovery of Small-Molecule Thermoresponsive Ionic Liquid Materials: A Review

Li,

Chu

2023

Molecules

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“…Abonia R et al [77] synthesized oxazole derivatives using imidazolium as an ionic liquid in the Suzuki Pd-mediated C-C coupling mechanism along with Piperidine-Appended Imidazolium [PAIM] [NTf2] ion as a specific ionic liquid Previously synthesised oxazoles and imidazoles are obtained via van Leusen synthesis and subjected to Suzuki Pd-catalyzed C-C coupling reactions. This mechanism is highly effective for synthesising imidazole and oxazole compounds with good yield.…”

Section: Synthesis Of Oxazoles Using Ionic Liquidsmentioning

confidence: 99%

Recent Development and Green Approaches for Synthesis of Oxazole Derivatives: A Review

Joshi¹,

Choudhary²

2022

IJPS

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Green Synthetic Methods Synthesis of Oxazole DerivativesThis review compiles green synthetic methods intended for the synthesis of oxazole derivatives. Oxazoles are a class of compounds with a wide range of biological activities. The application and biological activity of oxazoles is highly dependent on their structure. Now-a-days, scientists have been performing the synthesis of oxazole derivatives. High demands in synthesis often result in the production of various hazardous chemical substances. So, to minimize the production of toxic chemical substances, green synthetic approaches are used in this manner. Green synthesis covers different synthetic approaches, including the application of microwave techniques, ultrasound, ionic liquids, deep-eutectic solvents, the use of catalysts and continuous flow synthesis. In this review, the authors mentioned that not only these green synthetic approaches reduce the formation and utilisation of toxic chemicals, but there is an increase in the reaction performance that enhances the product yields, purity, post-synthetic processes and energy consumption when compared to conventional methods. Due to the biological and pharmacological significance of oxazoles and the demands of decreasing toxic solvents, catalysts, and energy consumption, this article gives a full literature survey on the significance of green synthetic methods in oxazole synthesis. It contains a literature survey over the period from 2010-2020. The emphasis of this article is its comprehensive literature survey on oxazole, which is helpful for the researchers working on the oxazole scaffold and gaining information on the green synthetic approaches to their synthesis.

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“…32 Besides elemental fluorine, the direct creation of a C–F bond could be accomplished by means of functional group inter-conversion of C–H or C–X bonds, mediated by numerous fluorinating agents. 27 b ,28 b ,31 b ,33 On the other hand, synthesis of OFs via the insertion of fluorinated groups into organic molecules has become highly attractive to preparative organic chemists. In this context, various fluoroalkylating reagents have been offered to bring a fluoroalkyl group ( e.g.…”

Section: Introductionmentioning

confidence: 99%

Site-selective nucleophilic substitution reactions of pentafluoropyridine with hydroxybenzaldehydes: synthesis of triarylmethanes comprising perfluoropyridine moieties

Vari,

Ranjbar-Karimi,

Mohammadiannejad

2023

New J. Chem.

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Ionic liquid-mediated synthesis and functionalization of heterocyclic compounds

Cited by 9 publications

References 302 publications

Expeditious Discovery of Small-Molecule Thermoresponsive Ionic Liquid Materials: A Review

Expeditious Discovery of Small-Molecule Thermoresponsive Ionic Liquid Materials: A Review

Recent Development and Green Approaches for Synthesis of Oxazole Derivatives: A Review

Site-selective nucleophilic substitution reactions of pentafluoropyridine with hydroxybenzaldehydes: synthesis of triarylmethanes comprising perfluoropyridine moieties

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