{[MIM-NO2]C(NO2)3} a unique nano ionic liquid: application to the synthesis of novel Biginelli-type compounds

Khazaei, Ardeshir; Alaie, Saied; Baghery, Saeed; Kaboudin, Babak; Bayat, Yadollah; Asgari, Asiye

doi:10.1039/c5ra24619a

Cited by 20 publications

(5 citation statements)

References 58 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The required reaction mixture, including {[MIMNO 2 ]C(NO 2 ) 3 } nanocatalyst, was stirred and provided high to excellent yields. Reusability of catalyst was mentioned for three subsequent cycles with insignificant decrease in activity . The said protocol makes the considerable improvements over classical Biginelli conditions.…”

Section: Nanocatalystsmentioning

confidence: 99%

See 1 more Smart Citation

Biginelli Reaction: Polymer Supported Catalytic Approaches

et al. 2019

View full text Add to dashboard Cite

The Biginelli product, dihydropyrimidinone (DHPM) core, and its derivatives are of immense biological importance. There are several methods reported as modifications to the original Biginelli reaction. Among them, many involve the use of different catalysts. Also, among the advancements that have been made to the Biginelli reaction, improvements in product yields, less hazardous reaction conditions, and simplified isolation of products from the reaction predominate. Recently, solid-phase synthetic protocols have attracted the research community for improved yields, simplified product purification, recyclability of the solid support, which forms a special economic approach for Biginelli reaction. The present Review highlights the role of polymer-supported catalysts in Biginelli reaction, which may involve organic, inorganic, or hybrid polymers as support for catalysts. A few of the schemes involve magnetically recoverable catalysts where work up provides green approach relative to traditional methods. Some research groups used polymer−catalyst nanocomposites and polymer-supported ionic liquids as catalyst. Solvent-free, an ultrasound or microwave-assisted Biginelli reactions with polymer-supported catalysts are also reported.

show abstract

Section: Nanocatalystsmentioning

confidence: 99%

“…Reusability of catalyst was mentioned for three subsequent cycles with insignificant decrease in activity. 246 The said protocol makes the considerable improvements over classical Biginelli conditions. The nano ionic liquid catalyst succeeded to reduce the reaction time notably with high yields at room temperature.…”

Section: Acs Combinatorial Sciencementioning

confidence: 99%

Biginelli Reaction: Polymer Supported Catalytic Approaches

et al. 2019

View full text Add to dashboard Cite

show abstract

“…Although the most direct process to synthesize DHPMs is multicomponent Biginelli condensation, this process often requires three starting materials in reacting to form a product in harsh conditions and affords in moderate yields of corresponding products . To overcome these drawbacks, various liquid and solid catalysts such as Bronsted acid, nanocatalyst, ionic liquids, carbon nanotubes, and metal organic framework have been developed. However, significant drawbacks remain as a result of undesirable side‐products, harsh conditions, expensive catalysts, or limitations of heterogeneous systems with volatile organic solvents and longer reaction times.…”

Section: Figurementioning

confidence: 99%

Au Nanorod: An Efficient Catalyst for One‐Pot Synthesis of 3,4‐Dihydropyrimidin‐2(1H)‐ones via the Multicomponent Biginelli Reaction.

Nguyen

et al. 2017

ChemistrySelect

View full text Add to dashboard Cite

Gold nanoparticle catalysts have attracted much attention due to their catalytic efficiency under mild conditions. We report here the synthesis of a series of shapes of gold nanocrystals by simple reduction of HAuCl4⋅3H2O and application them as the catalysts for multicomponent Biginelli reaction. Amongst these, unsupported gold nanorods show the best catalytic activity. Its efficiency allows one‐pot synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones to proceed in high yield under mild conditions.

show abstract

“…[28] The characters of obtained ILs in the terms of chemical and physical properties such as state of IL under ambient conditions, hydrophobicity, solubility, conductive activity, etc., are designable by pairing the different anions, cations and also alkyl substituted groups on the cations (Figure 1.13a). [29] A coulombic, hydrogen bonding and van der Waals interaction between cation and anion mainly determine the ILs behavior especially their ionicity, which affects the cohesive energy between the ions. [30] In 2010, Watanabe et al…”

Section: Ionic Liquids (Ils)mentioning

confidence: 99%

“…ILs are good media with viscosity and density higher than some general solvents and are also reusable. Deriving from their properties, ILs are therefore the one of attractive materials used in many fields, such as an exchange media, [29,32] catalysis [29] and electrical applications. [33][34][35] Attempt to use ILs as conducting materials was recently shown by Ven and coworker in 2013.…”

Section: Ionic Liquids (Ils)mentioning

confidence: 99%

Hybrid materials from covalent organic frameworks and ionic liquids

Maliyaem

View full text Add to dashboard Cite

Covalent organic frameworks (COFs) are new type material, whereby their wide range of properties derived from the chemistry of frameworks and their regular porosity. Here in, we reported the successful syntheses of the novel hybrid materials between porous COF material and ionic liquids (ILs). The crystalline porous powder of boroxine?based COF, so called COF?5, is reproducible via a condensation reaction between hexahydroxyltriphenylene and phenyldiboronic acid under a mild condition using a conventional heating method. The as?synthesized COF-5 was characterized with PXRD, FT-IR, TGA and BET techniques, showing that the material contained 1D regular channels caused by ?-? stacking of the gauze sheets with a surface area of 1700 m2 g?1. Ionic liquid, namely 1-vinyl-3-ethylimidazolium bromide (VEIM[Br]) and 1-vinyl-3-ethylimidazolium bis(trifluoromethanesulfonyl)imide (VEIM[NTf2]), were infiltrated into the pores of COF-5 comparing with a silica porous material SBA?15 and imine?based COF, named imine?1, using a vacuum infiltration method. The BET analysis of VEIM[Br]@COF?5 shows a decrease in surface area of 170 m2 g?1 along with the PXRD and TGA profile shows that 20 % of infiltrated IL are occupied in pore cavities without a disruption on the host structure. The in?situ polymerization of VEIM[Br] in porous material was carried out using thermal radical initiator in solvent?free condition under an inert atmosphere of nitrogen yielding a polyVEIM[Br]@COF-5. The BET surface area of 518 m2 g?1 implies the higher ordered?alignment of polymer of VEIM[Br] along the 1D-channel of COF?5. Moreover, the new hybrid material, VEIM[Br]@COF?5 was attempted to use as a heterogeneous catalyst in a cycloaddition of CO2 with propylene oxide. The result shows a turnover number (TON) of 64�within 20 hours and turnover frequency (TOF) of 3.2, which calculated from the measured conversions by 1H?NMR technique. Even through, the hybrid material is not yet be a high effective catalyst, but it has shed some light on the further development of new hybrid materials.

show abstract

{[MIM-NO₂]C(NO₂)₃} a unique nano ionic liquid: application to the synthesis of novel Biginelli-type compounds

Abstract: 1-Methyl-3-nitro-1H-imidazol-3-ium trinitromethanide {[MIM-NO2]C(NO2)3} as a novel and green NIL catalyst was synthesized, characterized and used to Biginelli reaction at room temperature under solvent-free conditions.

Cited by 20 publications

References 58 publications

Biginelli Reaction: Polymer Supported Catalytic Approaches

Biginelli Reaction: Polymer Supported Catalytic Approaches

Au Nanorod: An Efficient Catalyst for One‐Pot Synthesis of 3,4‐Dihydropyrimidin‐2(1H)‐ones via the Multicomponent Biginelli Reaction.

Hybrid materials from covalent organic frameworks and ionic liquids

Contact Info

Product

Resources

About