2-Hydroxyethylammonium acetate as a reusable and cost-effective ionic liquid for the efficient synthesis of bis(pyrazolyl)methanes and 2-pyrazolyl-1-nitroalkanes

2012 ◽  
Vol 90 (10) ◽  
pp. 798-804 ◽  
Author(s):  
Sara Sobhani ◽  
Razieh Nasseri ◽  
Moones Honarmand
Keyword(s):  
Ionic Liquid ◽  
Michael Reaction ◽  
Scale Up ◽  
Reaction Times ◽  
Cost Effective ◽  
Environmentally Benign ◽  
One Pot ◽  
High Yields ◽  
Reaction Media ◽  
Task Specific Ionic Liquid

A new and convenient method for the synthesis of bis(pyrazolyl)methanes by one-pot tandem Knoevenagel–Michael reaction of 3-methyl-1-phenyl-5-pyrazolone with aryl, heteroaryl, or alkyl aldehydes in the presence of 2-hydroxyethylammonium acetate (2-HEAA) as a task-specific ionic liquid is described. This method was also successfully applied for the synthesis of 2-pyrazolyl-1-nitroalkanes by Michael addition of 3-methyl-1-phenyl-5-pyrazolone with β-nitrostyrenes in short reaction times. The present protocol offers several advantages such as using a reusable and cost-effective ionic liquid, an environmentally benign reaction media, being amenable to scale-up and good to high yields of the products.

scholarly journals A Task-Specific Ionic-Liquid-Mediated Solvent-Free Protocol for Direct Access to Dimethyl Acetal Protected Benzimidazole 2-Carboxaldehydes

SynOpen ◽  
2020 ◽  
Vol 04 (04) ◽  
pp. 89-95
Author(s):  
Swapan Majumdar ◽  
Barnali Deb ◽  
Ankita Chakraborty ◽  
Jewel Hossain
Keyword(s):  
Ionic Liquid ◽  
Scale Up ◽  
Reaction Times ◽  
Dimethyl Acetal ◽  
Single Step ◽  
Direct Access ◽  
Imidazolium Ionic Liquid ◽  
Reaction Conditions ◽  
High Yields ◽  
Task Specific Ionic Liquid

AbstractA robust and straightforward protocol has been developed for the synthesis of a diverse array of dimethyl acetal protected benz­imidazole-2-carboxaldehydes by reacting various 2-amino aniline derivatives with methyl 4,4-dimethoxy-3-oxobutanoate using the task-specific­ imidazolium ionic liquid (HBIm·TFA) as a promoter for N-C/C-N annulation processes. The present protocol offers several advantages over existing protocols, such as single-step process, short reaction times, very mild reaction conditions, high yields, ease of purification, recovery and reusability of the catalyst, and scale-up of the reaction.

Ultrasound-assisted aqua-mediated synthesis of multi-substituted tetrahydropyridine-3-carboxylates using N-carboxymethyl-3-pyridinium hydrogensulfate ([N-CH2CO2H-3-pic]+HSO4−) as a new efficient ionic liquid catalyst

2021 ◽  
Vol 3 (6) ◽  
Author(s):  
Kobra Nikoofar ◽  
Fatemeh Shahriyari
Keyword(s):  
Ionic Liquid ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
H Nmr ◽  
Sonic Waves ◽  
Ft Ir ◽  
High Yields ◽  
Work Up ◽  
C Nmr

AbstractA simple, straightforward, and ultrasound-promoted method for the preparation of some highly functionalized tetrahydropyridines reported via pseudo five-component reaction of (hetero)aromatic aldehydes, different anilines, and alkyl acetoacetates in the presence of [N-CH2CO2H-3-pic]+HSO4−, as a novel ionic liquid, in green aqueous medium. The IL was synthesized utilizing simple and easily-handled substrates and characterized by FT-IR, 1H NMR, 13C NMR, GC-MASS, FESEM, EDX, and TGA/DTG techniques. The procedure contains some highlighted aspects which are: (a) performing the MCR in the presence of aqua and sonic waves, as two main important and environmentally benign indexes in green and economic chemistry, (b) high yields of products within short reaction times, (c) convenient work-up procedure, (d) preparing the new IL via simple substrates and procedure.

Ionic Liquid 4-(3-Methyl-1-imidazolio)-1-butanesulfonic Acid Hydrogen Sulfate-catalyzed Synthesis of Phthalazinetrione Derivatives

2012 ◽  
Vol 67 (7) ◽  
pp. 717-724
Author(s):  
Shihua Song ◽  
Xiang Deng ◽  
Zhi Guan ◽  
Yanhong He
Keyword(s):  
Ionic Liquid ◽  
Polyethylene Glycol ◽  
Condensation Reaction ◽  
Reaction Times ◽  
Solvent System ◽  
Environmentally Benign ◽  
Hydrogen Sulfate ◽  
One Pot ◽  
Simple Method ◽  
Peg 600

A simple method for the synthesis of phthalazinetrione derivatives by a one-pot three-component condensation reaction of phthalhydrazide, 1,3-dicarbonyl compounds and aldehydes catalyzed by the ionic liquid 4-(3-methyl-1-imidazolio)-1-butanesulfonic acid hydrogen sulfate ([BSO3HmIm]HSO4) is reported. Good to excellent yields were obtained in short reaction times in the solvent PEG 600 (polyethylene glycol 600) at 120 °C. The strategy proved to be efficient and environmentally benign. The catalyst/solvent system could easily be recovered and reused for at least 5 times without noticeable loss of activity

One Pot Three Component Synthesis of 9-arylpolyhydroacridine Derivatives in an Ionic Liquid Medium

2005 ◽  
Vol 2005 (9) ◽  
pp. 600-602 ◽  
Author(s):  
Yu-Ling Li ◽  
Mei-Mei Zhang ◽  
Xiang-Shan Wang ◽  
Da-Qing Shi ◽  
Shu-Jiang Tu ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Ammonium Acetate ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
One Pot ◽  
High Yields ◽  
Work Up ◽  
Ionic Liquid Medium

In this paper the preparation of 3,3,6,6-tetramethyl-9-aryl-1,2,3,4,5,6,7,8,9,10- decahydroacridin-1,8-dione derivatives from aromatic aldehydes, 5,5-dimethyl-1,3- cyclohexanedione and ammonium acetate in ionic liquids [bmim+][BF4-] is described. This new method has the advantages of easier work-up, milder reaction conditions, high yields and an environmentally benign procedure compared with other methods.

Ferric hydrogensulphate as a recyclable catalyst for the synthesis of fluorescein derivatives

2011 ◽  
Vol 65 (4) ◽  
Author(s):  
Hossein Eshghi ◽  
Narges Mirzaie
Keyword(s):  
Phthalic Anhydride ◽  
Scale Up ◽  
Reaction Times ◽  
Catalytic Amount ◽  
Recyclable Catalyst ◽  
Environmentally Benign ◽  
Absorption And Emission ◽  
Emission Properties ◽  
Benign Nature ◽  
High Yields

AbstractPolycondensation reactions of phenols with phthalic anhydride were carried out in the presence of ferric hydrogensulphate under melt conditions. The reactions proceeded in short reaction times by using a catalytic amount of Fe(HSO4)3 and the corresponding fluorescein derivatives were obtained in high yields. The simplicity, scale-up, along with the use of an inexpensive, non-toxic, recyclable catalyst of an environmentally benign nature, are other remarkable features of the procedure. The absorption and emission properties of these fluorescein derivatives were studied.

scholarly journals Synthesis of biscoumarin derivatives by the reaction of aldehydes and 4-hydroxycoumarin using ruthenium (III) chloride hydrate as a versatile homogeneous catalyst

2012 ◽  
Vol 77 (4) ◽  
pp. 407-413 ◽  
Author(s):  
Khalil Tabatabaeian ◽  
Hannaneh Heidari ◽  
Alireza Khorshidi ◽  
Manouchehr Mamaghani ◽  
Nosrat Mahmoodi
Keyword(s):  
Michael Reaction ◽  
Aqueous Media ◽  
Environmentally Benign ◽  
Homogeneous Catalyst ◽  
Reaction Conditions ◽  
One Pot ◽  
The One ◽  
High Yields ◽  
Chloride Hydrate ◽  
Short Times

The one-pot domino Knoevenagel-type condensation/Michael reaction of aromatic, heteroaromatic and aliphatic aldehydes with 4-hydroxycoumarin in aqueous media in the presence of ruthenium salt as homogeneous catalyst was investigated. It was found that 5 mol% of RuCl3.nH2O catalyzes biscoumarin synthesis in high yields (70-95%) under optimised, mild, green and environmentally benign reaction conditions in short times (25-35min).

scholarly journals Ultrasound Promoted Green and Facile One-Pot Multicomponent Synthesis of 3,4-dihydropyrano[c]chromene Derivatives

2013 ◽  
Vol 2013 ◽  
pp. 1-8 ◽  
Author(s):  
Ravikumar Nagalapalli ◽  
Satyanarayana Reddy Jaggavarapu ◽  
Venkata Prasad Jalli ◽  
Anand Solomon Kamalakaran ◽  
Gopikrishna Gaddamanugu
Keyword(s):  
Aqueous Media ◽  
Reaction Times ◽  
Environmentally Benign ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
High Yields

Ultrasound promoted mild one-pot multicomponent synthesis of 3,4-dihydropyrano[c]chromenes from 4-hydroxycoumarin, arylaldehydes and malononitrile was achieved in aqueous media. The methodology promises advantages of short reaction times, environmentally benign conditions, high yields, and operational convenience.

Facile synthesis of 3-arylidene-1,3-dihydroindol-2-ones catalysed by a Brønsted acidic ionic liquid

2008 ◽  
Vol 2008 (11) ◽  
pp. 642-643 ◽  
Author(s):  
Yi Hu ◽  
Hui Kang ◽  
Bi-Wen Zeng ◽  
Ping Wei ◽  
He Huang
Keyword(s):  
Ionic Liquid ◽  
High Purity ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Facile Synthesis ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
High Yields ◽  
Work Up

A series of 3-arylidene-1,3-dihydroindol-2-one derivatives were conveniently synthesised by the condensation of aromatic aldehydes with 1,3-dihydroindol-2-one using a Brønsted acidic ionic liquid as a dual solvent-catalyst. This method has the advantages of short reaction times, simple work-up, high yields with high purity, being environmentally benign and the ionic liquid can be reused.

scholarly journals [DBN][HSO4]-Promoted facile and green synthesis of 2-Amino-4H-pyrans derivatives under microwave irradiation

2021 ◽  
Vol 11 (2-S) ◽  
pp. 89-97
Author(s):  
Vishal Mane ◽  
Dhanjay Mane
Keyword(s):  
Ionic Liquid ◽  
Microwave Irradiation ◽  
Room Temperature ◽  
Knoevenagel Condensation ◽  
Reaction Times ◽  
Environmentally Benign ◽  
Successive Reaction ◽  
Solvent Free Conditions ◽  
High Yields ◽  
First Time

The [DBN][HSO4] -promoted Knoevenagel condensation followed by cyclization protocol has been developed for the first time by a successive reaction of aldehydes, dimedone and malononitrile to afford 2-Amino-4H-pyrans derivatives in high to excellent yields at room temperature. The synergic couple of microwave and ionic liquid provided the capability to allow a variability of functional groups, short reaction times, easy workup, high yields, recyclability of the catalyst, and solvent-free conditions, thus providing economic and environmental advantages. Keywords: [DBN][HSO4], Environmentally benign, 2-Amino-4H-pyrans, Knoevenagel condensation, Microwave irradiation

A highly effective and mild protocol for the production of 1-thioamidoalkyl-2-naphthols using 1,3-disulfonic acid imidazolium trifluoroacetate as a dual-functional catalyst

2018 ◽  
Vol 73 (5) ◽  
pp. 289-293 ◽  
Author(s):  
Mostafa Karami ◽  
Abdolkarim Zare
Keyword(s):  
Ionic Liquid ◽  
Reaction Time ◽  
Reaction Times ◽  
Solvent Free ◽  
Disulfonic Acid ◽  
One Pot ◽  
Mild Conditions ◽  
Dual Functional ◽  
Highly Effective ◽  
High Yields

AbstractA solvent-free protocol for the production of 1-thioamidoalkyl-2-naphthols via a one-pot multi-component reaction of arylaldehydes with 2-naphthol and thioacetamide using the ionic liquid 1,3-disulfonic acid imidazolium trifluoroacetate ([Dsim][TFA]) is described. Furthermore, a plausible and attractive mechanism based on the dual functionality of the catalyst is proposed. Because of the dual functionality of [Dsim][TFA] (possessing acidic and basic sites), it is found to be generally highly effective, affording the products in high yields and short reaction times under mild conditions. We claim that this is one of the best protocols for the synthesis of 1-thioamidoalkyl-2-naphthols (in terms of yield, temperature, conditions, and/or the reaction time).

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