Dicationic ionic liquids as effective catalysts in solvent free strecker synthesis

Verma, Khushboo; Sharma, Ashutosh; Badru, Rahul

doi:10.1016/j.crgsc.2021.100060

Cited by 10 publications

(4 citation statements)

References 23 publications

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“…Verma et al have proposed the utility of dicationic imidazolium-based ILs as effective catalysts for the Strecker synthesis of aminonitriles 89 from aromatic aldehydes 87 , aniline ( 88 ) and trimethylsilyl cyanide (TMSCN) at room temperature under solvent-free conditions (Scheme 27 ). 84 Herein, the ILs enhanced the nucleophilicity of 87 and helped in the generation of the nitrile ion from TMSCN. The synthesis of different imidazolium-based dicationic ILs was carried out using methyl imidazole and dibutyl chloride, and they were characterized using NMR, IR and TGA-DSC.…”

Section: Construction Of Heterocycles Catalyzed By Ionic Liquidsmentioning

confidence: 99%

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: Construction Of Heterocycles Catalyzed By Ionic Liquidsmentioning

confidence: 99%

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

“…Strecker reaction is one of the best known and investigated multicomponent reactions, which allows the synthesis of α-aminonitrile substrates through one-pot condensation of amine, carbonyl, and nitrile compounds [ 23 ]. Verma et al used for the first time DILs as catalysts in the Strecker synthesis starting from trimethylsilylcyanide (TMSCN), aniline, and differently substituted benzaldehydes ( Scheme 1 ) [ 24 ].…”

Section: Applications In Organocatalysismentioning

confidence: 99%

“… DILs catalyzed Strecker reaction: general reaction and structures of DILs used, reproduced with permission from [ 24 ]. …”

Section: Figures Schemes and Tablementioning

confidence: 99%

Recent Advances in Imidazolium-Based Dicationic Ionic Liquids as Organocatalysts: A Mini-Review

et al. 2022

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Imidazolium-based dicationic ionic liquids (DILs) are gaining considerable space in the field of organocatalysis mainly due to the opportunities in offering new possible applicable structural variations. In addition to the well-known variables which made the ionic liquids (ILs) famous as the type of cation and anion used, the nature of the molecular spacer moiety turns out a further possibility to improve some physicochemical properties, for example, solubility, acidity, electrochemical behavior, and so on. For this reason, this class of ionic liquids has been considered as possible competitors to their corresponding monocationic salts in replacing common catalysts in organic synthesis, particularly in cases in which their bidentate nature could positively affect the catalytic activity. This mini-review is intended to highlight the progress carried out in the last six years in the field of organocatalysis, including DILs as such and as hybrids with polymers, nanomaterials, and composites.

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“…Among these cyanide agents, TMSCN has proven to be relatively safe, easy to handle, highly soluble in organic solvents, and more effective as a cyanide anion source for the nucleophilic addition of imines under mild conditions compared to other cyanating reagents. In recent years, numerous methods have been developed for the synthesis of α-aminonitriles via Strecker reaction using TMSCN as a cyanide source catalyzed by various catalysts, such as MnO-doped Fe 3 O 4 NPs, [11] SiO 2 , [12] Fe 3 O 4 @SiO 2 core-shell MNPs, [13] natural halloysite nanotubes, [14] mandelic acid, [15] Fe 3 O 4 , [16] CeCl 3 , [17] MCM-41, [18] I 2 , [19] polymer, [20] g-C 3 N 4anchored sulfonic acid, [21] ionic liquids, [22] ZnO, [23] Cd-Fe 2 O 4 @SiO 2 @ZrO 2 /SO 4 2 -/Cu/Ni, [24] CMK-5-SO 3 H, [25] Fe 3 O 4 @SiO 2 -APTES-TFA, [26] S m I 3 , [27] Fe 3 O 4 @SiO 2 -NH 2 -GA, [28] metal organic framework (MOFs) [29] and covalent organic frameworks (COFs). [30] Although each of the above methods has its own merit, most of these methods are associated with certain disadvantages including the use of commercially unavailable metal catalysts, organic solvents, low yields and long reaction times.…”

mentioning

confidence: 99%

An Efficient and Rapid Synthesis of α-Aminonitriles via Strecker Reaction Catalyzed by Humic Acid

Xi,

Duan,

Chi

et al. 2023

Chinese Journal of Organic Chemistry

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An efficient one pot three-component Strecker reaction for the green synthesis of α-aminonitriles from carbonyl compounds, amines and trimethylsilyl cyanide (TMSCN) in the presence of a catalytic amount of humic acid catalyst under solvent-free conditions at room temperature has been developed. This methodology has advantages of high yield, no need for metal catalysts, short reaction time, mild reaction conditions, simple operation, green and reusable catalyst.

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Dicationic ionic liquids as effective catalysts in solvent free strecker synthesis

Cited by 10 publications

References 23 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

Recent Advances in Imidazolium-Based Dicationic Ionic Liquids as Organocatalysts: A Mini-Review

An Efficient and Rapid Synthesis of α-Aminonitriles via Strecker Reaction Catalyzed by Humic Acid

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