Choline based deep eutectic solvent mediated Friedlander annulation: A sustainable and regiospecific approach to polysubstituted quinoline

Singh, Rajkumar Romeshkumar; Devi, Thokchom Jeeta; Singh, Okram Mukherjee

doi:10.1016/j.crgsc.2022.100272

Cited by 5 publications

(5 citation statements)

References 28 publications

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“…Singh et al synthesized polysubstituted quinolines (38) from 2-aminobenzophenones (36) and ketones (37) using choline based deep eutectic solvent ILs through Friedlander annulation (Scheme 10). 66 The regiospecificity were observed with basic choline hydroxide based ILs, prepared from choline chloride and zinc chloride, along with moderate to excellent yields, where ILs played a dual role of solvent as well as catalysts. Without the loss of catalytic performance, ILs were reused up to three consecutive catalytic cycles.…”

Section: Cholinium Based Ilsmentioning

confidence: 98%

“…Furthermore, the catalyst exhibited minimal activity loss, allowing for its convenient recovery, separation, and reuse for up to three cycles. 67 Regiospecificity was observed with a basic choline hydroxide IL prepared from choline chloride and zinc chloride. Moderate to excellent yields were obtained and the IL played the dual role of solvent and catalyst.…”

Section: Ammonium Ionic Liquidsmentioning

confidence: 99%

“…Araya-Lopez and colleagues reported the dehydration of fructose (67) for the selective production of 5-hydroxymethyl furfural (175) catalyzed by triazole-based ILs supported on alumina (Scheme 60). 130 The triazoles were synthesized via a 1,3-dipolar cycloaddition, for example, using sodium 3-azidopropane-1-sulfonate and phenyl acetylene, with the adduct then being supported on alumina to form the triazolium-based IL.…”

Section: Scheme 59 Caffbail-catalyzed Synthesis Of Dihydropyrimidinon...mentioning

confidence: 99%

“…For the effective transformation of glucose (66) to 5-hydroxymethyfurfural (121) in water/1-octanol, Sun et al designed and synthesized the tetraimidazolyl ILs (Teim ILs), containing sulfonic acid as cation and aluminium tetrachloride as anion (Scheme 39). 99 Herein, Lewis and Brønsted acid promoted the isomerisation of66 to fructose afterwards its dehydration to121.The synthesis of these ILs were achieved by treating pentaerythritol with phosphorus tribromide followed by incorporation of imidazole and ionization using HCl and aluminium tetrachloride.…”

Section: Scheme 38mentioning

confidence: 99%

See 3 more Smart Citations

The Synthesis of Nitrogen- and Oxygen-Containing Heterocyclic Scaffolds Assisted by Ionic Liquids: A 2022 Literature Survey

Dhameliya,

Raghani,

Desai

et al. 2023

Synlett

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Heterocycles have gained recognition as vital components in approved drugs, drawing substantial attention from the scientific community. Ionic liquids (ILs) have been utilized for their transformative role in heterocycle synthesis, showcasing distinctive properties that are pivotal in diverse chemical transformations, while also acting as effective catalysts and offering safer alternatives to volatile organic solvents. This review delves into the synthesis of nitrogen- and oxygen-containing heterocyclic structures, employing various ILs such as ammonium, cholinium, DABCO-based, DBU-based, guanidinium, imidazolium, phosphonium, pyridinium, and miscellaneous. They have proven indispensable in facilitating reactions like Fischer-indole synthesis, Biginelli, Knoevenagel condensations and many more. Notably, the recyclability of ILs serves as a valuable asset, aiding in the completion of intricate synthetic pathways, multicomponent reactions, and one-pot syntheses, ultimately enhancing yields. This review seeks to guide researchers in selecting suitable ILs for specific chemical reactions, enabling the synthesis of aza- and/ or oxa-heterocycles described in 2022. This advancement holds promising prospects for drug development and other applications within the domain of heterocyclic chemistry.

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Section: Cholinium Based Ilsmentioning

confidence: 98%

Section: Ammonium Ionic Liquidsmentioning

confidence: 99%

Section: Scheme 59 Caffbail-catalyzed Synthesis Of Dihydropyrimidinon...mentioning

confidence: 99%

Section: Scheme 38mentioning

confidence: 99%

See 2 more Smart Citations

The Synthesis of Nitrogen- and Oxygen-Containing Heterocyclic Scaffolds Assisted by Ionic Liquids: A 2022 Literature Survey

Dhameliya,

Raghani,

Desai

et al. 2023

Synlett

View full text Add to dashboard Cite

show abstract

“…Many more plant‐derived metal and metal oxide nanoparticles have been used for biological, environmental, and industrial applications. For instance, Nickel oxide nanoparticles, [88] Platinum nanoparticles, [89] Palladium nanoparticles, [90] Aluminium oxide nanoparticles, [91] Silica nanoparticles, [92] Magnesium oxide nanoparticles, [93] and Cobalt nanoparticles [94] . Detailed discussion of these plant‐derived nanoparticles is beyond the scope of this review article.…”

Section: Production Of Metallic and Metal Oxide Nanoparticles (Nps) U...mentioning

confidence: 99%

Plant‐Derived Nanomaterials for Targeted Biological Applications and Smart Agriculture

Ghosh,

Yadav,

Sankaranarayanan

et al. 2023

ChemistrySelect

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Biologically inspired nanomaterials and nanotechnology have advanced in almost all scientific and technological research areas, including biomedical applications and agriculture. Nanomaterials hold immense potential for applications in biomedical and agricultural applications. By harnessing the natural capabilities of plants as sources of reducing and capping agents, the synthesis of nanomaterials becomes cost‐effective eco‐friendly, and yields biocompatible products. Here, we provide a comprehensive overview of various plant‐derived nanomaterials synthesized using different methods, highlighting their applications in biomedical and biological sciences, including bioimaging, biosensing, drug delivery, and therapeutics. Additionally, the impact of nanotechnology on precision agriculture is explored, showcasing recent advancements such as nanofertilizers, nanopesticides, nanobiosensors, and nanocarrier‐mediated delivery systems, which exhibit promising results. These recent developments underscore the transformative potential of nanotechnology in both biomedical and agriculture domains.

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Lewis Acid‐Promoted Domino Processes for the Synthesis of Homoallylic Amines, Quinolines and Tetrahydroquinolines

Vishwakarma,

Vodnala,

Musib

et al. 2024

Adv Synth Catal

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Herein, the synthesis of homoallylic amines, quinolines, and tetrahydroquinolines has been demonstrated. The domino one‐pot multi‐component approach has been accomplished using Lewis acid‐catalyzed conditions. A useful scaffold construction strategy can be achieved by controlling the electronic effect of aniline rather than relying on reaction conditions. The described method applies to a wide variety of substrates embedded with diverse functional groups and can be extended toward the synthesis of natural products. Suitable control experiments, real‐time NMR studies, and DFT calculations have validated the reported process. The protocol outlines a strategy for synthesizing homoallylic amines and quinolines, controlled by the electronic properties of anilines.

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Choline based deep eutectic solvent mediated Friedlander annulation: A sustainable and regiospecific approach to polysubstituted quinoline

Cited by 5 publications

References 28 publications

The Synthesis of Nitrogen- and Oxygen-Containing Heterocyclic Scaffolds Assisted by Ionic Liquids: A 2022 Literature Survey

The Synthesis of Nitrogen- and Oxygen-Containing Heterocyclic Scaffolds Assisted by Ionic Liquids: A 2022 Literature Survey

Plant‐Derived Nanomaterials for Targeted Biological Applications and Smart Agriculture

Lewis Acid‐Promoted Domino Processes for the Synthesis of Homoallylic Amines, Quinolines and Tetrahydroquinolines

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