Preparation of neutral ionic liquid [2-Eim] OAc with dual catalytic-solvent system roles for the synthesis of 2-amino-3-cyano-7-hydroxy-4-(aryl)-4H-chromene derivatives

Ghorbani, Mahdi; Noura, Soheila; Oftadeh, Mohsen; Soleimani, Mohammad Haji; Behbodi, Kazem

doi:10.1016/j.molliq.2015.09.024

Cited by 35 publications

(7 citation statements)

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“…After optimizing the experimental conditions, the efficiency of the Fe 3 O 4 @PS‐Arg MNPs as catalyst for the synthesis of other chiral chromene derivatives was evaluated by reaction of ß ‐naphthol, malononitrile and other aromatic aldehyde derivatives (Scheme ). In all studied cases, Fe 3 O 4 @PS‐Arg MNPs gave the corresponding products 4a–j better than the previously reported catalysts by comparison of yields, reaction time and enantioselectivity (Table ).…”

Section: Resultsmentioning

confidence: 59%

“…Several methods have been previously reported for the one‐pot synthesis of chromene derivatives using diverse catalyst systems such as Na 2 CO 3 under grinding, K 2 CO 3, DBU, chitosan, tungstic acid‐SBA‐15, potassium phthalimide‐ N ‐oxyl (POPINO), amino appended β‐ cyclodextrins ( β‐ CDs), Fe (HSO 4 ) 3, Fe 3 O 4 ‐chitosan nanoparticles, amino‐silane modified Fe 3 O 4 nanoparticles (MNPs‐NH 2 ), [2‐Eim]OAc, nano‐sized MgO, TPOP‐2, KSF, and Mg/Al‐HT, etc.…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective synthesis of 3‐amino‐1‐aryl‐1H‐benzo[f]chromene‐2‐carbonitrile derivatives by Fe₃O₄@PS‐arginine as an efficient chiral magnetic nanocatalyst

Karkhah

Kefayati

Shariati

2019

Applied Organom Chemis

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A novel chiral magnetic nanocatalyst was prepared by the surface modification of Fe3O4 magnetic nanoparticles (MNPs) with a chloropropylsilane and further by arginine to form Fe3O4@propylsilan‐arginine (Fe3O4@PS‐Arg). After the structural confirmation of Fe3O4@PS‐Arg synthesized MNPs by Fourier transform‐infrared, X‐ray diffraction, field emission‐scanning electron microscopy, transmission electron microscopy, vibrating‐sample magnetometry and thermogravimetric analyses, their catalytic activity was evaluated for one‐pot enantioselective synthesis of 3‐amino‐1‐aryl‐1H‐benzo[f]chromene‐2‐carbonitrile derivatives. The results showed that in the presence of 0.07 g Fe3O4@PS‐Arg nanocatalyst and ethanol as solvent, the best reaction yield (96%) was obtained in the least time (5 min). Easy operation, reusability and stability, short reaction time, high reaction yields and good enantioselectivity are the major advantages of the newly synthesized nanocatalyst. Also, this study provides a novel strategy for further research and investigation on the synthesis of new reusable enantioselective catalysts and chiral compounds.

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Section: Resultsmentioning

confidence: 59%

Section: Introductionmentioning

confidence: 99%

Enantioselective synthesis of 3‐amino‐1‐aryl‐1H‐benzo[f]chromene‐2‐carbonitrile derivatives by Fe₃O₄@PS‐arginine as an efficient chiral magnetic nanocatalyst

Karkhah

Kefayati

Shariati

2019

Applied Organom Chemis

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“…The group has prepared 4 H ‐chromene derivatives by the three‐component condensation reaction of aldehydes 1 , malononitrile 2 , and resorcinol 7 in the presence of the neutral ionic liquid (10 mol%) maintaining the temperature 67.5°C and under solvent‐free condition (Scheme 19). [ 109 ] Applying the method, a wide range of 4 H ‐chromene derivatives 8 were synthesized and the yield was found up to 96% taking the time 22–29 min. Furthermore, the used catalyst was further recycled and reused to carry out the reactions four times.…”

Section: Ionic Liquid‐based Synthesis Of 2‐amino‐4h‐chromenesmentioning

confidence: 99%

Ionic liquid‐assisted synthesis of 2‐amino‐3‐cyano‐4H‐chromenes: A sustainable overview

Chatterjee¹,

Bhukta²,

Dandela³

2021

Journal of Heterocyclic Chem

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In advanced research, the role of ionic liquid is gradually enhanced as an alternative finding. For a long time, many strategies have been developed based on the ionic liquid conveying the role of greener solvents or catalysts. In the case of multi‐component synthesis, ionic liquids have a wide range of applications to revise a method in a sustainable and greener approach. The last two decades have given a number of methods to achieve the 4H‐chromene derivatives by applying different types of ionic liquids. Especially, 2‐amino‐3‐cyano‐4H‐chromene moiety that exhibits pharmacological and biological activity, have been synthesized using simple or functionalized ionic liquids such as basic, acidic, neural, metal‐tagged, or carbon‐oriented ionic liquid. In this review, we have concised the multicomponent reactions that have been reported to synthesize the 4H‐chromene derivatives following the versatility of ionic liquids.

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“…Chromene ring is formed in the presence of some inorganic and organic catalysts, such as K2CO3 in water [23], Ca (OH)2 [24], nano ZnO [25], nanocrystalline MgO in aqueous media [26], silica gel supported polyamine [27], ammonium acetate [28], and potassium phthalimide [29]. Some ionic liquids are also used as catalysts for this purpose, for example, OAc [30], basic ionic liquids from triethylenetetramine or ethylenediamine, and TFA (trifluoroacetic acid) [31]. Monodisperse Pd nanomaterials anchored graphene oxide [32] and bimetallic Pd-Ru/graphene oxide-based catalysts [33] are also applied in the one-pot three-component synthesis of 2-amino-4H-chromene derivatives.…”

Section: Introductionmentioning

confidence: 99%

Study on the Synthesis of Some (Un)Substituted 2-Amino-4-aryl-7-hydroxy-4H-chromene-3-carbonitriles in the Water Medium

Thành

Hai

Hien

et al. 2018

22nd International Electronic Conference on Synthetic Organic Chemistry

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Preparation of neutral ionic liquid [2-Eim] OAc with dual catalytic-solvent system roles for the synthesis of 2-amino-3-cyano-7-hydroxy-4-(aryl)-4H-chromene derivatives

Cited by 35 publications

References 50 publications

Enantioselective synthesis of 3‐amino‐1‐aryl‐1H‐benzo[f]chromene‐2‐carbonitrile derivatives by Fe₃O₄@PS‐arginine as an efficient chiral magnetic nanocatalyst

Enantioselective synthesis of 3‐amino‐1‐aryl‐1H‐benzo[f]chromene‐2‐carbonitrile derivatives by Fe₃O₄@PS‐arginine as an efficient chiral magnetic nanocatalyst

Ionic liquid‐assisted synthesis of 2‐amino‐3‐cyano‐4H‐chromenes: A sustainable overview

Study on the Synthesis of Some (Un)Substituted 2-Amino-4-aryl-7-hydroxy-4H-chromene-3-carbonitriles in the Water Medium

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Preparation of neutral ionic liquid [2-Eim] OAc with dual catalytic-solvent system roles for the synthesis of 2-amino-3-cyano-7-hydroxy-4-(aryl)-4H-chromene derivatives

Cited by 35 publications

References 50 publications

Enantioselective synthesis of 3‐amino‐1‐aryl‐1H‐benzo[f]chromene‐2‐carbonitrile derivatives by Fe3O4@PS‐arginine as an efficient chiral magnetic nanocatalyst

Enantioselective synthesis of 3‐amino‐1‐aryl‐1H‐benzo[f]chromene‐2‐carbonitrile derivatives by Fe3O4@PS‐arginine as an efficient chiral magnetic nanocatalyst

Ionic liquid‐assisted synthesis of 2‐amino‐3‐cyano‐4H‐chromenes: A sustainable overview

Study on the Synthesis of Some (Un)Substituted 2-Amino-4-aryl-7-hydroxy-4H-chromene-3-carbonitriles in the Water Medium

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Enantioselective synthesis of 3‐amino‐1‐aryl‐1H‐benzo[f]chromene‐2‐carbonitrile derivatives by Fe₃O₄@PS‐arginine as an efficient chiral magnetic nanocatalyst

Enantioselective synthesis of 3‐amino‐1‐aryl‐1H‐benzo[f]chromene‐2‐carbonitrile derivatives by Fe₃O₄@PS‐arginine as an efficient chiral magnetic nanocatalyst