Facile, high-yielding preparation of pyrrolidinium, piperidinium, morpholinium and 2,3-dihydro-1H-isoindolinium salts and ionic liquids from secondary amines

RSC Advances ◽  
2014 ◽  
Vol 4 (44) ◽  
pp. 23327-23337 ◽  
Author(s):  
Antony J. Ward ◽  
Anthony F. Masters ◽  
Thomas Maschmeyer

High yield and purity heterocyclic salts and ionic liquids can be obtained via the microwave irradiation of equimolar amounts of a secondary amine and an α,ω-dibromoalkane in water in the presence of K2CO3 followed by anion exchange.

2010 ◽  
Vol 8 (4) ◽  
pp. 946-952 ◽  
Author(s):  
Hadi Marwani

AbstractIn this study, spectroscopic investigation of chiral and achiral room temperature ionic liquids is achieved. New ionic liquids were prepared via metathesis, accomplished by the reaction of either L-phenylalanine ethyl ester hydrochloride, chlorpromazine hydrochloride or 1,10-Phenanthroline monohydrate hydrochloride with lithium bis(trifluoromethane) sulfonamide in water. The resulting ionic liquids were produced in high yield and purity. The results obtained by use of 1H NMR and IR experiments were in very good agreement with the chemical structures of the synthesized ionic liquids. In addition, the results of thermal gravimetric analysis suggested that these ionic liquids have good thermal stability. UV-Vis and fluorescence spectroscopy measurements indicated that these ionic liquids are strongly optically absorbent and fluorescent. Lastly, time-based fluorescence steady-state measurements demonstrated the high photostability of these ionic liquids.


2020 ◽  
Vol 16 ◽  
pp. 168-174
Author(s):  
Jucleiton J R Freitas ◽  
Queila P S B Freitas ◽  
Silvia R C P Andrade ◽  
Juliano C R Freitas ◽  
Roberta A Oliveira ◽  
...  

The propargylation of aldehydes promoted by microwave irradiation using allenylboron compounds in a chemo- and regioselective way is described. The corresponding products were obtained in short reaction time, high yield and purity without the need of any solvent when allenylboronic acid pinacol ester was used, or using a minimal amount of acetone when potassium allenyltrifluoroborate was used.


2019 ◽  
Author(s):  
Jucleiton J R Freitas ◽  
Queila P S B Freitas ◽  
Silvia R C P Andrade ◽  
Juliano C R Freitas ◽  
Roberta A Oliveira ◽  
...  

The propargylation of aldehydes promoted by microwave irradiation using allenyl boron compounds in a chemo- and regioselective way is described. The corresponding products were obtained in short reaction time, high yield and purity without the need of any solvent when allenyl boronic acid pinacol ester was used, or using a minimal amount of acetone when potassium allenyl trifluoroborate was used.


Author(s):  
Mahesh G. Kharatmol ◽  
Deepali Jagdale

Pyrazoline class of compounds serve as better moieties for an array of treatments, they have antibacterial, antifungal, antiinflammatory, antipyretic, diuretic, cardiovascular activities. Apart from these they also have anticancer activities. So, pertaining to its importance, many attempts are made to synthesize pyrazolines. Since conventional methods of organic synthesis are energy and time consuming. There are elaborate pathways for green and eco-friendly synthesis of pyrazoline derivatives including microwave irradiation, ultrasonic irradiation, grinding and use of ionic liquids which assures the synthesis of the same within much lesser time and by use of minimal energy


2019 ◽  
Vol 16 (7) ◽  
pp. 1024-1031
Author(s):  
Diparjun Das ◽  
Kalyani Rajkumari ◽  
Lalthazuala Rokhum

Aim and Objective: Sustainable production of fine chemicals both in industries and pharmaceuticals heavily depends on the application of solid-phase synthesis route coupled with microwave technologies due to their environmentally benign nature. In this report, a microwave-assisted esterification reaction using polymer-bound triphenylphosphine and 4,4′-dinitroazobenzene reagent system was investigated. Materials and Methods: The solvents were obtained from Merck India. Polymer-bound triphenylphosphine (~3 mmol triphenylphosphine moiety/g) was acquired from Sigma-Aldrich. The progress of the reaction was observed by thin-layer chromatography. All the reactions were performed in Milestones StartSYNTH microwave. The NMR spectra were recorded on Bruker Avance III 300, 400, and 500 MHz FT NMR Spectrometers. Using azo compound and polymer-bound triphenyl phosphine as a coupling reagent, esterification of different carboxylic acids with alcohols was performed under microwave irradiation. Results: Esterification of benzoic acid with 1-propanol under microwave irradiation gave a high yield of 92% propyl benzoate in 60 minutes only. Isolation of the ester products was relatively simple as both the byproducts polymer-bound triphenylphosphine oxide and hydrazine could be removed by simple filtration. The rates of reactions were found to be directly proportional to the pKa of the benzoic acids. Conclusion: 4,4′-Dinitroazobenzene was introduced as a novel coupling reagent, in conjugation with polymer-bound triphenylphosphine, for esterification reactions under microwave irradiation. The low moisture sensitivity of the reaction system, easy separation of the byproducts, and column chromatographyfree isolation of esters help our methods with application significance, particularly from the ‘Sustainable Chemistry’ perspective.


2020 ◽  
Vol 7 (3) ◽  
pp. 183-195
Author(s):  
Musa Özil ◽  
Emre Menteşe

Background: Benzoxazole, containing a 1,3-oxazole system fused with a benzene ring, has a profound effect on medicinal chemistry research owing to its important pharmacological activities. On the other hand, the benzoxazole derivative has exhibited important properties in material science. Especially in recent years, microwave-assisted synthesis is a technique that can be used to increase diversity and quick research in modern chemistry. The utilization of microwave irradiation is beneficial for the synthesis of benzoxazole in recent years. In this focused review, we provide a metaanalysis of studies on benzoxazole in different reaction conditions, catalysts, and starting materials by microwave technique so far, which is different from conventional heating. Methods: Synthesis of different kind of benzoxazole derivatives have been carried out by microwave irradiation. The most used method to obtain benzoxazoles is the condensation of 2-aminophenol or its derivatives with aldehydes, carboxylic acids, nitriles, isocyanates, and aliphatic amines. Results: Benzoxazole system and its derivatives have exhibited a broad range of pharmacological properties. Thus, many scientists have remarked on the importance of the synthesis of different benzoxazole derivatives. Conventional heating is a relatively inefficient and slow method to convey energy in orientation to the reaction medium. However, the microwave-assisted heating technique is a more effective interior heating by straight coupling of microwave energy with the molecules. Conclusion: In this review, different studies were presented on the recent details accessible in the microwave- assisted techniques on the synthesis of the benzoxazole ring. It presents all examples of such compounds that have been reported from 1996 to the present. Benzoxazoles showed an extensive class of chemical substances not only in pharmaceutical chemistry but also in dyestuff, polymer industries, agrochemical, and optical brighteners. Thus the development of fast and efficient achievement of benzoxazoles with a diversity of substituents in high yield is getting more noteworthy. As shown in this review, microwave-assisted synthesis of benzoxazoles is a very effective and useful technique.


2021 ◽  
Vol 11 (10) ◽  
pp. 4659
Author(s):  
Eun-Jung Kim ◽  
Gyu-Min Im ◽  
Chang-Soo Lee ◽  
Yun-Gon Kim ◽  
Byoung Joon Ko ◽  
...  

The calcium-binding protein S100A9 regulates inflammatory processes and the immune response. It is overexpressed in a variety of inflammatory and oncologic conditions. In this study, we produced a recombinant human S100A9 (hS100A9) antigen with high yield and purity and used it to generate a hybridoma cell culture-based monoclonal anti-hS100A9 antibody. We selected five anti-hS100A9 antibodies from cell supernatants that showed high antigen binding efficiency and identified the nucleotide sequences of three antibodies: two with high effective concentration values and one with the lowest value. The antigen and antibody development procedures described herein are useful for producing large amounts of monoclonal antibodies against hS100A9 and other antigens of interest. The nucleotide sequences of the anti-hS100A9 monoclonal antibody revealed herein will be helpful in the generation of recombinant antibodies or antibody fragments against hS100A9.


2021 ◽  
Vol 12 ◽  
pp. 204173142110086
Author(s):  
Jun Yong Kim ◽  
Won-Kyu Rhim ◽  
Yong-In Yoo ◽  
Da-Seul Kim ◽  
Kyoung-Won Ko ◽  
...  

Exosomes derived from mesenchymal stem cells (MSCs) have been studied as vital components of regenerative medicine. Typically, various isolation methods of exosomes from cell culture medium have been developed to increase the isolation yield of exosomes. Moreover, the exosome-depletion process of serum has been considered to result in clinically active and highly purified exosomes from the cell culture medium. Our aim was to compare isolation methods, ultracentrifuge (UC)-based conventional method, and tangential flow filtration (TFF) system-based method for separation with high yield, and the bioactivity of the exosome according to the purity of MSC-derived exosome was determined by the ratio of Fetal bovine serum (FBS)-derived exosome to MSC-derived exosome depending on exosome depletion processes of FBS. The TFF-based isolation yield of exosome derived from human umbilical cord MSC (UCMSC) increased two orders (92.5 times) compared to UC-based isolation method. Moreover, by optimizing the process of depleting FBS-derived exosome, the purity of UCMSC-derived exosome, evaluated using the expression level of MSC exosome surface marker (CD73), was about 15.6 times enhanced and the concentration of low-density lipoprotein-cholesterol (LDL-c), known as impurities resulting from FBS, proved to be negligibly detected. The wound healing and angiogenic effects of highly purified UCMSC-derived exosomes were improved about 23.1% and 71.4%, respectively, with human coronary artery endothelial cells (HCAEC). It suggests that the defined MSC exosome with high yield and purity could increase regenerative activity.


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