A Phosphine-mediated Synthesis of 2,3,4,5-tetra-substituted Nhydroxypyrroles from α-oximino Ketones and Dialkyl Acetylenedicarboxylates Under Ionic Liquid Green-media

2018 ◽  
Vol 21 (1) ◽  
pp. 14-18
Author(s):  
Ashraf S. Shahvelayati ◽  
Maryam Ghazvini ◽  
Khadijeh Yadollahzadeh ◽  
Akram S. Delbari
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Organic Solvents ◽  
Condensation Reaction ◽  
Reaction Medium ◽  
Sustainable Chemistry ◽  
Polyfunctional Compounds ◽  
High Yields ◽  
Work Up ◽  
Reaction Media

Background: The development of multicomponent reactions (MCRs) in the presence of task-specific ionic liquids (ILs), used not only as environmentally benign reaction media, but also as catalysts, is a new approach that meet with the requirements of sustainable chemistry. In recent years, the use of ionic liquids as a green media for organic synthesis has become a chief study area. This is due to their unique properties such as non-volatility, non-flammability, chemical and thermal stability, immiscibility with both organic compounds and water and recyclability. Ionic liquids are used as environmentally friendly solvents instead of hazardous organic solvents. Objective: We report the condensation reaction between α-oximinoketone and dialkyl acetylene dicarboxylate in the presence of triphenylphosphine to afford substituted pyrroles under ionic liquid conditions in good yields. Result: Densely functionalized pyrroles was easily prepared from reaction of α-oximinoketones, dialkyl acetylene dicarboxylate in the presence of triphenylphosphine in a quantitative yield under ionic liquid conditions at room temperature. Conclusion: In conclusion, ionic liquids are indicated as a useful and novel reaction medium for the selective synthesis of functionalized pyrroles. This reaction medium can replace the use of hazardous organic solvents. Easy work-up, synthesis of polyfunctional compounds, decreased reaction time, having easily available-recyclable ionic liquids, and good to high yields are advantages of present method.

Synthesis of 1,8-dioxo-octahydro-xanthene and tetrahydrobenzo[b]pyran derivatives promoted by two bis-imidazolium-based ionic liquids

2021 ◽  
Vol 08 ◽  
Author(s):  
Maryam Shirzad ◽  
Mitra Nasiri ◽  
Nader Daneshvar ◽  
Farhad Shirini ◽  
Hassan Tajik
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Knoevenagel Condensation ◽  
Reaction Rates ◽  
Xanthene Derivatives ◽  
Acidic Ionic Liquids ◽  
Dicationic Ionic Liquids ◽  
Acidic Nature ◽  
Work Up ◽  
Reaction Media

Aim and objective: In this work, we have prepared two bis-dicationic ionic liquids with the same cationic core (Bis-imidazole) and different counter-anions using sulfuric acid and perchloric acids. After that, the efficiency and ability of these compounds as catalysts were investigated and compared in the promotion of Knoevenagel condensation and synthesis of benzo[b]pyran derivatives to see the effect of the anionic counter-part in the reaction. Material and method: In a 25 mL round-bottomed flask, a mixture of aldehyde (1.0 mmol), 1,3-cyclodicarbonyl (2.0 mmol) and the desired amount of the mentioned acidic ionic liquids was heated at 90°C in the absence of solvent (Reaction A) or In a 25 mL round-bottomed flask, a mixture of aldehyde (1.0 mmol), 1,3-cyclodicarbonyl (1.0 mmol), malononitrile, (1.1 mmol) and optimized amounts of the ionic liquid in water (3.0 mL) was heated at 80°C (Reaction B) for the appropriated time. After the completion of the reactions which were monitored by TLC (n-hexane: EtOAc; 3:1), 10 mL of water was added and the mixture was stirred for 2 minutes. Then, the products were separated by filtration and were washed several times with water. After drying, the pure products were obtained while there was no need to further. Results: Comparison of the obtained results from both of the ionic liquids revealed that [H2-Bisim][HSO4]2 because of its more acidic structure had a more catalytic activity for the preparation of 1,8-dioxo-octahydro-xanthene derivatives but [H2-Bisim][ClO4]2 was relatively more efficient for the synthesis of tetrahydrobenzo[b]pyran derivatives since the stronger acidic nature of [H2-Bisim][HSO4]2 may prevent the simple activation of malononitrile in the reaction media. Conclusion: In this study, we have introduced efficient methods for the synthesis of 1,8-dioxo-octahydro-xanthene and tetrahydrobenzo[b]pyran derivatives in the presence of catalytic amounts of [H2-Bisim][ClO4]2 and [H2-Bisim][HSO4]2 These methods have several advantages such as ease of preparation and handling of the catalysts, high reaction rates, excellent yields, eco-friendly procedures and simple work-up.

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.

Ionic Liquid Promoted Eco-friendly and Efficient Synthesis of Six-membered Npolyheterocycles

2018 ◽  
Vol 15 (8) ◽  
pp. 1124-1146 ◽  
Author(s):  
Navjeet Kaur
Keyword(s):  
Organic Chemistry ◽  
Ionic Liquid ◽  
Ionic Liquids ◽  
Organic Solvents ◽  
Review Article ◽  
Environmentally Benign ◽  
Wide Range ◽  
Catalyzed Reactions ◽  
Metal Catalyzed ◽  
Reaction Media

Background: The synthesis of N-polyheterocycles by environmentally benign method is highly attractive but challenging proposition. New strategies have been developed for the preparation of polycyclic heterocycles in the last decades. In this review article, the synthesis of nitrogen containing six-membered polycyclic heterocyclic compounds is presented with the application of ionic liquids. This contribution focuses on the literature related to the total synthesis of six-membered N-polyheterocycles. Objective: Ionic liquids not only acted as environmentally benign reaction media but also as catalysts which afforded the very promising replacements of traditional molecular solvents in organic chemistry due to their stability, non-flammability, non-volatility and ease of recyclability. Ionic liquids are utilized in metal catalyzed reactions in place of organic solvents in the last years. It has attracted considerable attention in recent years. Ionic liquids acted as alternatives of organic solvents and these ILs are environment friendly. Conclusion: In the area of green chemistry ionic liquid assisted synthesis is a very promising technique which afforded a flexible platform for the formation of heterocycles. The influence of ILs on the development of efficient and new synthetic protocols over the last decade for the construction of N-polyheterocycles is featured in this review article. These synthetic strategies will continue to attract more attention and will find a wide range of applications in organic synthesis. In conclusion, ionic liquids assisted syntheses have become an efficient and powerful tool in organic chemistry quickly.

Efficient regio- and stereo-selective cleavage of aziridines and epoxides using an ionic liquid as reagent and reaction medium

2007 ◽  
Vol 85 (5) ◽  
pp. 366-371 ◽  
Author(s):  
Brindaban C Ranu ◽  
Laksmikanta Adak ◽  
Subhash Banerjee
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Organic Solvent ◽  
Reaction Medium ◽  
Synthetic Route ◽  
High Yields

Ionic liquids, containing a variety of functionalities such as halo, azido, and thiocyano, efficiently cleave aziridines and epoxides to the corresponding products in high yields. The cleavages are regio- and stereo-selective. The reactions are complete in 1 h at 60 °C and do not require any other catalyst or organic solvent. Thus, a convenient synthetic route to 1,2-haloamines, 1,2-azidoamines, 1,2-thiocyanoamines, 1,2-azidoalcohols, and 1,2-thiocyanoalcohols is developed.Key words: aziridine, epoxide, ionic liquid, cleavage, regioselectivity, stereoselectivity

scholarly journals Polyborane reactions in ionic liquids

2006 ◽  
Vol 78 (7) ◽  
pp. 1349-1355 ◽  
Author(s):  
Yuqi Li ◽  
Upal Kusari ◽  
Patrick J. Carroll ◽  
Mark G. Bradley ◽  
Larry G. Sneddon
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Organic Solvents ◽  
Reaction Medium ◽  
High Yield ◽  
Insertion Reactions ◽  
Cage Compounds ◽  
Alkyne Insertion

In contrast to reactions that have been observed in traditional organic solvents, decaborane olefin-hydroboration and alkyne-insertion reactions proceed in ionic liquid (IL) solvents without the need of a catalyst. These reactions now provide important new, high-yield synthetic pathways to functionalized decaborane and ortho-carborane clusters. As illustrated by the synthesis of n-B18H22, ILs can also provide an inert reaction medium for carrying out dehydrocondensation reactions leading to higher fused cage compounds.

Heteropoly acid in ionic liquid — An efficient and recyclable system for one-pot three-component Mannich reaction

2007 ◽  
Vol 85 (1) ◽  
pp. 77-80 ◽  
Author(s):  
Meghana S Rasalkar ◽  
Sachin V Bhilare ◽  
Amol R Deorukhkar ◽  
Nitin B Darvatkar ◽  
Manikrao M Salunkhe
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Organic Solvents ◽  
Mannich Reaction ◽  
Heteropoly Acid ◽  
Phosphotungstic Acid ◽  
Reaction Medium ◽  
Homogeneous Reaction ◽  
Ambient Conditions ◽  
One Pot

This paper describes a one-pot three-component Mannich reaction, catalyzed by phosphotungstic acid (H3PW12O40), a heteropoly acid in ionic liquid. The catalyst was found to be mild and efficient, and the protocol affords β-amino ketones in good yields under ambient conditions. Several ionic liquids and conventional organic solvents were employed for the reaction. The ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF4) offered the best results in terms of yield of the products. It was observed that a homogeneous reaction medium proved beneficial for the yield of the reaction.Key words: Mannich reaction, β-amino ketones, phosphotungstic acid, ionic liquid, recyclability.

Green preparation of quinoline derivatives through FeCl3·6H2O catalyzed Friedlander reaction in ionic liquids

2004 ◽  
Vol 82 (7) ◽  
pp. 1192-1196 ◽  
Author(s):  
Jianji Wang ◽  
Xuesen Fan ◽  
Xinying Zhang ◽  
Lijun Han
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Condensation Reaction ◽  
Reaction Medium ◽  
Iron Chloride ◽  
Quinoline Derivatives ◽  
Reaction Conditions ◽  
Environmental Friendliness ◽  
Operating Process ◽  
Chloride Hexahydrate

The preparation of substituted quinoline derivatives through a Friedlander condensation reaction utilizing the ionic liquid [bmim][BF4] as the reaction medium and iron chloride hexahydrate (FeCl3·6H2O) as a catalyst is described. The advantages in using this method include its environmental friendliness, simple operating process in both mild and neutral reaction conditions, and good yields.Key words: ionic liquid, Friedlander reaction, quinoline derivatives, green chemistry.

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.

Acceleration of Baylis-Hillman reaction using ionic liquid supported organocatalyst

2021 ◽  
Vol 08 ◽  
Author(s):  
Vivek Srivastava
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Reaction Rate ◽  
Reaction Medium ◽  
Catalyst Loading ◽  
Catalyst Recycling ◽  
Catalytic Systems ◽  
Heterogeneous Catalytic ◽  
Highly Active ◽  
Low Catalyst Loading

Background: Baylis-Hillman reaction suffers from the requirement of cheap starting materials, easy reaction protocol, possibility to create the chiral center in the reaction product has increased the synthetic efficacy of this reaction, and high catalyst loading, low reaction rate, and poor yield. Objective: The extensive use of various functional or non-functional ionic liquids (ILs) with organocatalyst increases the reaction rate of various organic transformations as a reaction medium and as a support to anchor the catalysts. Methods: In this manuscript, we have demonstrated the synthesis of quinuclidine-supported trimethylamine-based functionalized ionic liquid as a catalyst for the Baylis-Hillman reaction. Results: We obtained the Baylis-Hillman adducts in good, isolated yield, low catalyst loading, short reaction time, broad substrate scope, accessible product, and catalyst recycling. N-((E,3S,4R)-5-benzylidene-tetrahydro-4-hydroxy-6-oxo-2H-pyran-3-yl) palmitamide was also successfully synthesized using CATALYST-3 promoted Baylis-Hillman reaction. Conclusion: We successfully isolated the 25 types of Baylis-Hillman adducts using three different quinuclidine-supported ammonium-based ionic liquids such as Et3AmQ][BF4] (CATALYST-1), [Et3AmQ][PF6] (CATALYST-2), and [TMAAmEQ][NTf2](CATALYST-3) as new and efficient catalysts. Tedious and highly active N-((E,3S,4R)-5-benzylidene-tetrahydro-4-hydroxy-6-oxo-2H-pyran-3-yl) palmitamide derivative was also synthesized using CATALYST-3 followed by Baylis-Hillman reaction. Generally, all the responses demonstrated higher activity and yielded high competition with various previously reported homogenous and heterogeneous Catalytic systems. Easy catalyst and product recovery followed by six catalysts recycling were the added advantages of the prosed catalytic system.

InCl3·4H2O-promoted green preparation of xanthenedione derivatives in ionic liquids

2005 ◽  
Vol 83 (1) ◽  
pp. 16-20 ◽  
Author(s):  
Xuesen Fan ◽  
Xueyuan Hu ◽  
Xinying Zhang ◽  
Jianji Wang
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Green Synthesis ◽  
Novel Method ◽  
Green Procedure ◽  
Reaction Media ◽  
Operational Simplicity

A green procedure for the synthesis of xanthenedione derivatives (3) through InCl3·4H2O-promoted condensation of aldehydes (1) and 5,5-dimethyl-1,3-cyclohexanedione (2) in ionic liquids is described in this paper. This novel method has such advantages as operational simplicity and environmental benignancy together with enhanced atom utilization. Moreover, the reaction media and the catalyst can be recovered conveniently and reused effectively for at least six times.Key words: ionic liquid, xanthenedione derivatives, indium trichloride, green synthesis.

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