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.

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 Cs2CO3/[bmim]Br as an Efficient, Green, and Reusable Catalytic System for the Synthesis of N-Alkyl Derivatives of Phthalimide under Mild Conditions

2008 ◽  
Vol 2008 ◽  
pp. 1-4 ◽  
Author(s):  
Alireza Hasaninejad ◽  
Abdolkarim Zare ◽  
Ahmad Reza Moosavi-Zare ◽  
Fatemeh Khedri ◽  
Rahimeh Rahimi ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Catalytic System ◽  
Reaction Times ◽  
Catalytic Amount ◽  
Conjugate Addition ◽  
Reaction Conditions ◽  
Mild Conditions ◽  
Alkyl Derivatives ◽  
High Yields ◽  
Derivatives Of

Aza-conjugate addition of phthalimide to α,β-unsaturated esters efficiently achieves in the presence of catalytic amount of Cs2CO3 and ionic liquid 1-butyl-3-methylimidazolium bromide ([bmim]Br) under mild reaction conditions (70°C) to afford N-alkyl phthalimides in high yields and relatively short reaction times.

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.

scholarly journals Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones

2017 ◽  
Vol 13 ◽  
pp. 694-702 ◽  
Author(s):  
Gabriel P Costa ◽  
Natália Seus ◽  
Juliano A Roehrs ◽  
Raquel G Jacob ◽  
Ricardo F Schumacher ◽  
...  
Keyword(s):  
Reaction Times ◽  
Cycloaddition Reactions ◽  
Reaction Conditions ◽  
Keto Esters ◽  
Efficient Access ◽  
High Yields ◽  
Short Times

The use of sonochemistry is described in the organocatalytic enamine–azide [3 + 2] cycloaddition between 1,3-diketones and aryl azidophenyl selenides. These sonochemically promoted reactions were found to be amenable to a range of 1,3-diketones or aryl azidophenyl selenides, providing an efficient access to new ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones in good to excellent yields and short reaction times. In addition, this protocol was extended to β-keto esters, β-keto amides and α-cyano ketones. Selanyltriazoyl carboxylates, carboxamides and carbonitriles were synthesized in high yields at short times of reaction under very mild reaction conditions.

Ionic liquid promoted and mediated green preparation of arylbispyranylmethane and pyran derivatives and their hybrid with a pyrimidine nucleoside

2009 ◽  
Vol 2009 (8) ◽  
pp. 473-477 ◽  
Author(s):  
Xinying Zhang ◽  
Yingying Qu ◽  
Xuesen Fan ◽  
Xia Wang ◽  
Jianji Wang
Keyword(s):  
Ionic Liquid ◽  
High Efficiency ◽  
Reaction Medium ◽  
Environmentally Benign ◽  
Pyrimidine Nucleoside ◽  
Reaction Conditions ◽  
Operation Process ◽  
Antiviral Activities ◽  
Benign Nature ◽  
High Yields

The utilisation of an ionic liquid-[bmim][BF4] as both reaction medium and promoter for the reaction between aldehyde and 4-hydroxy-6-methylpyran-2-one is described. Without any added catalyst, this reaction was realised efficiently to give arylbispyranylmethane derivatives in high yields. Alternatively, when this reaction was carried out in the presence of acetic anhydride, fused pyran derivatives were obtained. These two novel procedures have advantages such as an environmentally benign nature, high efficiency, simple operation process and mild reaction conditions. As an application, these procedures were used in the preparation of novel 5-substituted pyrimidine nucleoside derivatives with potential antiviral activities.

scholarly journals The Role Ionic Liquid [BMIM][PF6] in One-Pot Synthesis of Tetrahydropyran Rings through Tandem Barbier–Prins Reaction

Molecules ◽  
2019 ◽  
Vol 24 (11) ◽  
pp. 2084
Author(s):  
Poliane K. Batista ◽  
João Marcos G. de O. Ferreira ◽  
Fabio P. L. Silva ◽  
Mario L. A. A Vasconcellos ◽  
Juliana A. Vale
Keyword(s):  
Ionic Liquid ◽  
Yield Loss ◽  
Allyl Bromide ◽  
Reaction Times ◽  
Prins Reaction ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Barbier Reaction ◽  
Significant Yield

Tetrahydropyran (THP) rings are common in several natural products, therefore, various strategies are being developed to synthesize these rings. The present work described the study of a one-pot synthesis of 2,4,6-trisubstituted tetrahydropyran compounds promoted by the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate [BMIM][PF6] through a Barbier–Prins reaction between allyl bromide and aldehydes. The use of [BMIM][PF6] gave Prins products from several aldehydes in good yields and reaction times. We also found that the anion, PF6-, accelerates the Barbier reaction when used alone, and the excess SnBr2 from the reaction conditions of the Barbier reaction leads to the formation of the THP rings, thus acting as a catalyst for Prins cyclization. Additionally, we demonstrate that ionic liquid can be recovered and reused five times in the preparation of 4-bromo-tetrahydro-2,6-diphenyl-2H-pyran without significant yield loss.

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 Infrared Irradiation-Assisted Multicomponent Synthesis of 2-Amino-3-cyano-4H-pyran Derivatives

2017 ◽  
Vol 56 (2) ◽  
Author(s):  
Arturo Sánchez ◽  
Fernando Hernández ◽  
Paulo César Cruz ◽  
Yolanda Alcaraz ◽  
Joaquín Tamariz ◽  
...  
Keyword(s):  
Ethyl Acetoacetate ◽  
Present Method ◽  
Reaction Times ◽  
Ammonium Hydroxide ◽  
Infrared Irradiation ◽  
Efficient Synthesis ◽  
Multicomponent Synthesis ◽  
Reaction Conditions ◽  
High Yields ◽  
Pyran Derivative

A simple, versatile, and efficient synthesis of 4<em>H</em>-pyran derivative compounds is achieved via a three-component cyclocondensation of aldehydes, malononitrile, and ethyl acetoacetate, using ammonium hydroxide as the catalyst, promoted by infrared irradiation. The present method offers several advantages, such as high yields, non hazardous reaction conditions as well as short reaction times.

scholarly journals One-pot, three-component synthesis of pyrrolo[2,3-d]pyrimidine derivatives

2018 ◽  
Vol 62 (1) ◽  
Author(s):  
Jabbar Khalafy ◽  
Ramin Javahershenas
Keyword(s):  
Simple Procedure ◽  
Reaction Times ◽  
Pyrimidine Derivatives ◽  
Reaction Conditions ◽  
One Pot ◽  
General Applicability ◽  
Green Approach ◽  
Three Component Reaction ◽  
High Yields ◽  
Work Up

<p>A green approach for the synthesis of polyfunctionalized pyrrolo[2,3-<em>d</em>]pyrimidine derivatives was successfully achieved by a one-pot, three-component reaction of arylglyoxals, 6-amino-1,3-dimethyluracil and barbituric acid derivatives in the presence of tetra-<em>n</em>-butylammonium bromide (TBAB) (5 mol%) as the catalyst in ethanol at 50 °C. This protocol has many advantages such as high yields (73-95%), green and simple procedure, short reaction times, easy work-up, mild reaction conditions and general applicability.</p>

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