- Biocompatible Ionic Liquid Promote One-Pot Synthesis of 2-Amino-4H-Chromenes Under Ambient Conditions
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Abstract: The synthesis of 2-amino-4H-chromenes through one-pot multicomponent reactions has received great attention due to the high atom efficiency and the broad bioactivities of the products. Here, the catalytic performances of a series of functional ionic liquids towards this type of reaction were investigated and the results showed that the ionic liquid, choline acetate ([Choline][Ac]), could efficiently promote this reactions under room temperature without the necessary of organic solvents. The reaction is easy to be conducted and the following work-up procedures are very simple. The pure products can be obtained through extraction and washing procedures, no column separation procedures are needed. Intriguingly, this reaction system can be easily scaled up to multi-gram, suggesting its perspective in industrial applications. In addition, the ionic liquid [Choline][Ac] can be easily prepared from cheap and biocompatible materials, and it can be feasibly recycled and reutilized for at least five cycles. Graphic Abstract: Various aldehydes, malononitrile and activated phenols could be converted to thecorresponding 2-amino-4H-chromenes with good to excellent isolated yields underthe catalysis of choline acetate at room temperature. [Figure not available: see fulltext.]
- Zhu, Anlian,Li, Qixing,Feng, Wanlu,Fan, Dongshuang,Li, Lingjun
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p. 720 - 733
(2020/08/07)
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- Cleaner enzymatic production of biodiesel with easy separation procedures triggered by a biocompatible hydrophilic ionic liquid
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The great challenges of modern industry and the environment make it important to develop sustainable energy resources with low cost. In this work, a cleaner enzymatic procedure for biodiesel production was developed through the utilization of a biocompatible and hydrophilic ionic liquid [Choline][H2PO4]. This ionic liquid can be synthesized from cheap raw materials through simple neutralization procedures, and it has been proved to be well biocompatible. The utilization of this ionic liquid in Novozym 435 catalyzed biodiesel production makes the reaction and work-up procedures very simple, because its hydrophilicity can lead to the implementation of a pseudo homogeneous reaction and then heterogeneous separation. Various oil resources such as triolein, sunflower oil and castor oil can all be converted to biodiesels with high yields. After the completion of reaction, both the ionic liquid and Novozym 435 can be recycled and reutilized for at least five cycles without a significant activity decrease. In addition, this reaction system can be conveniently scaled up to the multi-gram level with high efficiency and feasible separation. Overall, the above mentioned benefits make this ionic liquid based enzymatic system cleaner for the production of biodiesel and promising for further industrial applications.
- Chen, Qianhan,Cheng, Shuang,Fan, Dongshuang,Feng, Wanlu,Guo, Yuanyang,Li, Lingjun,Li, Zhiyong,Wang, Jianji,Zhu, Anlian
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p. 1944 - 1951
(2020/04/09)
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- Cytotoxicity of protic ionic liquids towards the HaCat cell line derived from human skin
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In this work we have investigated the toxicity of 10 PILs, consisting of ethyl-, ethanol-, diethanol- and triethanolammonium cations paired with nitrate, formate, acetate and glycolate anions. Their toxicity was quantified by the EC50 values of each of these PILs towards HaCat cells, which are derived from human skin cells. Additional salts and solvents were used for comparison including DMSO, choline chloride, potassium nitrate, sodium acetate and ethanol to distinguish if the toxicity changes were due to ionicity, short chain amphiphilic behaviour, or specific ion effects. The toxicity followed the general trend of choline chloride acetate containing PILs DMSO sodium acetate ethanol nitrate containing PILs or salt. Ethanolammonium acetate and ethylammonium acetate were identified as having the lowest toxicities of the PILs, being slightly more toxic than choline chloride or DMSO. Overall the toxicity was found to be highly dependent on the cation and anion combination, with the anion having a stronger affect. It was evident that the PILs can be tailored to vary their toxicities, and this is expected to be dependent on which cell lines are used.
- Abraham, Amanda N.,Arunkumar, Radhika,Drummond, Calum J.,Greaves, Tamar L.,Shukla, Ravi
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- Hydroxyl alkyl ammonium ionic liquid assisted green and one-pot regioselective access to functionalized pyrazolodihydropyridine core and their pharmacological evaluation
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Herein our team explored a promising synthetic trail to Functionalized pyrazolodihydropyridine core using hydroxyl alkyl ammonium ionic liquid via one-pot fusion of 3-methyl-1-phenyl-1H-pyrazole-5-amine, different heterocyclic aldehydes and 1, 3-Cyclic diones. The aimed compounds were obtained by Domino-Knoevenagel condensation and Michael addition followed by cyclization. The reaction transformation involves the formation of two C–C and one C–N bond formation. The perspective of the present work is selectively approached to Functionalized pyrazolodihydropyridine core excluding other potential parallel reactions under environmentally benign reaction condition. The present protocol show features such as the low E-factor, ambiphilic behavior of ionic liquid during reaction transformation, scale-up to a multigram scale, reusability of the ionic liquid, mild reaction condition, and produce water as a byproduct. All newly derived compounds were evaluated for their in vitro biological activities. In preliminary biological studies compound, 4c showed better potency than the standard drug ampicillin against Gram-negative bacteria (E. coli); the compound 4i exhibited outstanding activity against S. aeruginosa which is far better than ampicillin, chloramphenicol, and ciprofloxacin. The compound 4m was found more potent against C. albicans, than that of griseofulvin and show equipotency to nystatin whereas, in preliminary antitubercular screening, compound 4o was exhibited more potency than rifampicin. Noteworthy compounds 4f and 4i were found most active in antiproliferative screening.
- Patel, Divyang M.,Sharma, Mayank G.,Vala, Ruturajsinh M.,Lagunes, Irene,Puerta, Adrián,Padrón, José M.,Rajani, Dhanji P.,Patel, Hitendra M.
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p. 137 - 150
(2019/01/30)
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- The hydrophilic ionic liquid at room temperature and its use
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PROBLEM TO BE SOLVED: To provide a novel ionic liquid that is liquid at a room temperature and is hydrophilic, particularly water-soluble, and use thereof.SOLUTION: This invention provides a hydrophilic room-temperature ionic liquid including a cation and an anion, the cation being a quaternary ammonium cation of the formula (I), and the anion being a carboxylate anion, where R represents a 1-5C straight-chain or branched-chain alkylene group, and n represents an integer of 1-3.
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Paragraph 0105; 0106
(2019/09/11)
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- The Synthesis of 2,11-Diamino-4,9-diphenyl-4,9-dihydrobenzo [f] pyrano[3,2-h]chromene-3,10-dicarbonitrile Derivatives using Triethanolammonium Acetate as a Green Ionic Liquid
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Triethanolammonium acetate [TEA][HOAc] was used as a green ionic liquid and successfully utilized for the multi-component synthesis of 2,11-diamino-4,9-diphenyl-4,9-dihydrobenzo[f]pyrano[3,2-h]chromene-3,10-dicarbonitrile derivatives as new compounds by the reaction of 2,3-naphthalenediol with malononitrile and various aldehydes. Mild reaction conditions and high yields are some of the advantages of this method. These compounds were identified by IR, NMR spectroscopy and mass analysis.
- Khazaei, Ardeshir,Bashirian, Ehsan,Ranjbaran, Azam,Khazaei, Marzieh,Moosavi-Zare, Ahmad Reza
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p. 757 - 763
(2017/07/25)
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- BIOCATALYST SOLVENT USING IONIC LIQUID, AND BIOCATALYST SOLUTION CONTAINING THE SOLVENT AND BIOCATALYST
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PROBLEM TO BE SOLVED: To provide: a biocatalyst solvent that can be stored for a long period of time and that can dissolve a high concentration of a biocatalyst from low temperatures to high temperatures while retaining the activity of the biocatalyst; and a biocatalyst solution using the biocatalyst solvent. SOLUTION: The biocatalyst solvent is composed of an ionic liquid containing anions and quaternary ammonium cations represented by the following formula (1), where each Ra independently represents: a hydroxyalkyl group which has at least one hydroxyl group, in which the alkyl moiety is in a C1-10 straight-chained or branched state, and in which the alkyl moiety may contain an oxygen atom; a carboxyalkyl group which has at least one carboxy group, in which the alkyl moiety is in a C1-10 straight-chained or branched state, and in which the alkyl moiety may contain an oxygen atom; or a hydroxy-carboxyalkyl group which has at least one each of a hydroxyl group and a carboxy group, in which the alkyl moiety is in a C1-10 straight-chained or branched state, and in which the alkyl moiety may contain an oxygen atom and where each Rb independently represents a hydrogen atom or a C1-5 straight-chained or branched alkyl group. n represents an integer of 1-4. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0103-0105; 0108; 0109
(2016/10/10)
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- Preparation of protic ionic liquids with minimal water content and 15N NMR study of proton transfer
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Low-molecular-weight Bronsted acids and amine bases were used to reproducibly prepare very dry, high-purity room-temperature protic ionic liquids (PILs). A series of eight amine bases and six Bronsted acids were combined to produce 48 mixtures, of which 18 were liquid at room temperature. The phase transitions and thermal decomposition temperatures were determined for each mixture; whereas viscosity, density and conductivity were determined for the room-temperature liquids. By utilising 15N NMR it was possible to distinguish between neutral and ionised amine bases (ammonia vs. ammonium-type ion), which indicated that the protic ionic liquids were completely ionised when made as a stoichiometric mixture. However, a Walden plot comparison of fluidity and molar conductivity indicated the majority of PILs had much lower conductivity than predicted by viscosity unless the base contained excess proton-donating groups. This disparity is indicative of protic ionic molecules forming neutral aggregates or non-Newtonian fluid hydrogen-bonded networks with a secondary Grotthuss proton-hopping mechanism arising from polyprotic bases. the Owner Societies 2010.
- Burrell, Geoffrey L.,Burgar, Iko M.,Separovic, Frances,Dunlop, Noel F.
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body text
p. 1571 - 1577
(2010/08/05)
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