- Structures and single crystal to single crystal transformations of cadmium frameworks using a flexible tripodal ligand
-
A highly flexible tris-imidazole ligand N(CH2-m-C6H4-CH2-imidazole)3 (L) constructed using a tris(xylyl) backbone was synthesized. Its reactions with three cadmium(ii) salts gave various Cd(ii) coordination polymers, namely [CdL2](ClO4)2 (1), [CdLCl2] (2), and [CdL(OAc)2] (3). X-ray studies revealed that 1 crystallized in the trigonal space group R3 with high symmetry, while 2 and 3 crystallized in lower symmetrical space groups due to Cd-anion coordination. The flexibility of ligand L was evidenced in these structures, showing different conformations of L upon coordination and crystallization. In addition, complex [CdL2]Cl2 (4) was obtained by the anion exchange of 1 with sodium chloride via a single crystal to single crystal transformation. Similar to 1, complex 4 also crystallized in the trigonal space group R3 with a = 13.0945(3), b = 37.4353(10), and V = 5559.2(2). Importantly, this single crystal to single crystal transformation is crucial to afford this Cd(ii) coordination polymer with unbound Cl- anions, as the direct reaction of L and CdCl2 gives complex 2 with Cd-bound Cl-. This work shows the importance of flexible ligands in constructing various coordination polymer structures through the regulation of anions.
- Zhang, Zongyao,Xu, Lijin,Cao, Rui
-
-
Read Online
- Study of preparation and thermal stability of cyano-functionalized imidazolium type ionic liquids
-
Sixteen imidazolium type cyano-functionalized Br?nsted acidic ionic liquids with HSO4- and H2PO4 - anion were prepared adopting twostep method and were characterized by FT-IR, 1H and 13C NMR. The onse
- Liang,Li,Gou,Wang
-
-
Read Online
- Physicochemical and thermodynamic properties of imidazolium ionic liquids with nitrile and ether dual functional groups
-
Synthesis of new dual functionalized imidazolium ionic liquids (ILs) containing nitrile functionality and ether group were synthesized and characterized. Bis(trifluoromethylsulfonyl)imide, trifluoroacetate and dicyanamide were used as the anion. The combination of two functional groups on an imidazolium cation was mainly developed to assess their potential in desulfurization of fuel oil. Although ILs based on this individual functional group has been reported to improve the desulfurization efficiency, no effort has been made to combine nitrile and ether functional groups on the same cation to enhance the desulphurization potential. In this report, we tailored both nitrile and ether functionality on imidazolium cation and studied their physicochemical properties in details. NMR (1H and 13C) spectroscopy and elemental analysis were used to characterize the synthesized ILs. Physical properties and optical properties of the ILs were investigated in a wide temperature range. The synthesized ILs showed good thermal stability. COSMO-RS was effectively utilized to discuss the σ surface, σ potential and σ profile of the synthesized ILs.
- Raj, Jaganathan Joshua,Wilfred, Cecilia Devi,Shah, Syed Nasir,Pranesh, Matheswaran,Abdul Mutalib,Lethesh, Kallidanthiyil Chellappan
-
-
Read Online
- Effect of Structural Variations on the Thermophysical Properties of Protic Ionic Liquids: Insights from Experimental and Computational Studies
-
In this work, new protic ionic liquids (PILs) based on 1-methylimidazolium/1-propanenitrileimidazolium cations with hydrogen sulfate, methanesulfonate, trifluoromethanesulfonate, para-toluenesulfonate, trifluoroacetate, and acetate anions were synthesized. The structures and purity of the products were confirmed by using 1H and 13C NMR and CHNS elemental analysis. The effect of structural variations on the thermophysical properties, namely, refractive index, density, and viscosity, was evaluated in a wide temperature range. The viscosity and density values were measured within the temperature range of 293.15-373.15 K. The density values were used further to calculate more properties like thermal expansion coefficient, molecular volume, standard entropy, and the lattice energy. Moreover, the experimental values of viscosity were used for the calculation of activation energy. Refractive indices were measured within the temperature range of 293.15-323.15 K, and these values were also used in the calculation of electronic polarizability. Acid numbers of the prepared PILs were measured and correlated with their structure moiety. In addition, the density functional theory (DFT) calculations were performed to get a deeper insight into the effect of structural variations of the ion pairs on their physical properties.
- Khan, Amir Sada,Man, Zakaria,Bustam, Mohamad Azmi,Gonfa, Girma,Chong, Fai Kait,Ullah, Zahoor,Nasrullah, Asma,Sarwono, Ariyanti,Ahmad, Pervaiz,Muhammad, Nawshad
-
-
Read Online
- Thermophysical properties of a new dicationic ionic liquid
-
A new functionalized dicationic ionic liquid was synthesized with the final aim of studying its application in the extraction of metal ions in the mineral industry. In light of this application, the density, refractive index, and dynamic viscosities have been determined and correlated as a function of temperature. Density data were used to calculate the volumetric properties of the ionic liquid. Several empirical equations were used to evaluate the correlation between the density and refractive indices. The results show that the modified Eykman equation has the best fit. In addition, thermal behavior was measured by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC), and a high thermal stability and a wide liquid phase range were determined.
- Claros, Martha,Galleguillos, Hector R.,Brito, Ivan,Graber, Teofilo A.
-
-
Read Online
- Thermophysical properties of dual functionalized imidazolium-based ionic liquids
-
In this work, some new dual functionalized imidazolium-based ionic liquids 3-(3-butyl-1H-imidazol-3-ium-1-yl)propanenitrile chloride [C2CNBim] Cl, 3-(3-allyl-1H-imidazol-3-ium-1-yl)propanenitrile chloride [C 2CNAim]Cl, 3-[3-(2-hydrox
- Muhammad, Nawshad,Man, Zakaria,Ziyada, Abobakr K.,Bustam, M. Azmi,Mutalib, M. I. Abdul,Wilfred, Cecilia D.,Rafiq, Sikander,Tan, Isa Mohd
-
-
Read Online
- Thermophysical properties of 1-propyronitrile-3-alkylimidazolium bromide ionic liquids at temperatures from (293.15 to 353.15) K
-
In the present work, a series of 1-propyronitrile-3-alkylimidazolium bromide ionic liquids ([C2CN Cnim]Br, where n = 4, 6, 8, and 10) were synthesized and characterized using Fourier transform infrared spectroscopy (FTIR), NMR, and elemental analysis. Physical properties such as density, viscosity, and refractive index are measured and reported for a temperature range of (293.15 to 353.15) K and at atmospheric pressure. The influence of the alkyl chain on these properties is discussed. The present synthesized ionic liquids show a weak temperature dependency on the thermal expansion coefficient.
- Ziyada, Abobakr K.,Wilfred, Cecilia D.,Bustam, M. Azmi,Man, Zakaria,Murugesan, Thanapalan
-
-
Read Online
- A Novel zwitterionic imidazolium-based ionic liquid surfactant: 1-carboxymethyl-3-dodecylimidazolium inner salt
-
A novel zwitterionic imidazolium-based ionic liquid (IL) surfactant, 1-carboxymethyl-3-dodecylimidazolium inner salt, was synthesized. The molecule structure was confirmed by means of electrospray ionization mass spectrometry, 1H nuclear magnetic resonance and elemental analysis. The isoelectric point (pI) is 3.8 ± 0.1 at 35 ± 0.1 °C. The other important physicochemical parameters such as the critical micelle concentration (CMC), the surface tension at CMC (γCMC), the adsorption efficiency (pC 20), the surface pressure at CMC (ΠCMC), the maximum surface excess (Γm), the minimum molecular cross-sectional area (A min), the value of CMC/C 20 and the average number of aggregation (N m) were determined by surface tension and steady-state fluorescence probe methods, respectively. AOCS 2011.
- Liu, Xue-Feng,Dong, Li-Li,Fang, Yun
-
-
Read Online
- Synthesis and self-aggregation of a hydroxyl-functionalized imidazolium-based ionic liquid surfactant in aqueous solution
-
This paper deals with the synthesis and self-aggregation of a hydroxyl-functionalized imidazoliumbased ionic liquid (IL) surfactant, namely 1-hydroxyethyl-3-dodecylimidazolium chloride ([C2OHC 12im]Cl). The molecular structure was confirmed by means of electrospray ionization mass spectrometry (ESI-MS), 1H nuclear magnetic resonance (1H NMR) and elemental analysis. Many important physicochemical parameters, such as the critical micelle concentration (CMC), the surface tension at CMC (γCMC), the adsorption efficiency (pC20), the surface pressure at CMC (ΠCMC), the maximum surface excess (Γm), the minimum molecular cross-sectional area (Amin), the value of CMC/C20, the average number of aggregation (Nm) and the micellar microenvironment polarity were determined by surface tension-concentration curves, fluorescence spectra, and electrical conductivity. The phenomena of the second CMC, the concentration dependence of Nm, and the critical average aggregation number (N m,c) of imidazolium-based IL surfactants are reported for the first time in this paper. AOCS 2010.
- Liu, Xue-Feng,Dong, Li-Li,Fang, Yun
-
-
Read Online
- One-pot solvent-free microwave-assisted aza-Michael addition reaction of acrylonitrile
-
A novel and highly effective one-pot microwave-assisted aza-Michael addition reaction of acrylonitrile, as Michael acceptor with various primary aliphatic and aromatic amines, as Michael donor has been reported. The reaction was catalyzed by a cost-effective, highly efficient and eco-friendly catalyst, molecular sieve of 4 A0 size, under solvent-free conditions. A detail investigation on reaction controlling parameters like reaction timing and amount of catalyst was studied. The plausible mechanistic pathway has been proposed for the formation of acrylonitrile adducts. The identity of the synthesized products was established by conventional spectroscopic techniques FT-IR, 1H and 13C{1H} NMR, ESI-MS and DLS measurements. DLS result shows hydrodynamic diameter of lower alkyl chain in the range of 200–300 nm and for higher alkyl chain around 1 μm. Sheldon's hot filtration test confirms the significance of the catalyst and their heterogeneity was also confirmed by recycling it for five consecutive cycles without any noticeable change in the yield.
- Das, Parineeta,Devi, Nirmala,Puzari, Amrit
-
-
- Synthetic method N - cyanoethyl imidazole compound
-
The N - cyanoethyl imidazole compound is prepared from imidazoles and derivatives thereof as raw materials and acrylonitrile as Michael addition acceptors, and is free of catalysts. The N - cyanoethyl imidazole compound is synthesized in a solvent-free and air atmosphere at a high yield in a one-step method. The method is simple to operate, environmentally friendly, economical and practical, stable in performance and wide in product market. The reaction does not need special post-treatment, no by-product is generated, and the method is suitable for industrial production.
- -
-
Paragraph 0028-0032
(2021/10/16)
-
- Solvent- and Catalyst-Free Aza-Michael Addition of Imidazoles and Related Heterocycles
-
This work demonstrates the scope and limitations of the aza-Michael addition of imidazoles and related heterocycles with electron deficient olefins under solvent- and catalyst-free conditions. The reaction proceeds at 80 °C within hours towards completion as long as the azole derivative is sufficiently soluble in the Michael acceptor, which has been used in small excess. Workup only comprises evaporation of surplus Michael-acceptor, and no additional solvents are necessary for purifying the products.
- Gobec, Florian,Kodolitsch, Katharina,Slugovc, Christian
-
-
- KOtBu-Catalyzed Michael Addition Reactions Under Mild and Solvent-Free Conditions
-
Designed transition metal complexes predominantly catalyze Michael addition reactions. Inorganic and organic base-catalyzed Michael addition reactions have been reported. However, known base-catalyzed reactions suffer from the requirement of solvents, additives, high pressure and also side-reactions. Herein, we demonstrate a mild and environmentally friendly strategy of readily available KOtBu-catalyzed Michael addition reactions. This simple inorganic base efficiently catalyzes the Michael addition of underexplored acrylonitriles, esters and amides with (oxa-, aza-, and thia-) heteroatom nucleophiles. This catalytic process proceeds under solvent-free conditions and at room temperature. Notably, this protocol offers an easy operational procedure, broad substrate scope with excellent selectivity, reaction scalability and excellent TON (>9900). Preliminary mechanistic studies revealed that the reaction follows an ionic mechanism. Formal synthesis of promazine is demonstrated using this catalytic protocol.
- Thiyagarajan, Subramanian,Krishnakumar, Varadhan,Gunanathan, Chidambaram
-
supporting information
p. 518 - 523
(2020/02/04)
-
- Efficient protocol for Aza-Michael addition of N-heterocycles to α,β-unsaturated compound using [Ch]OH and [n-butyl urotropinium]OH as basic ionic liquids in aqueous/solvent free conditions
-
The present work emphasizes on a green methodology using designed and synthesized basic ionic liquid, [n-butyl Urotropinium]OH, and commercially available aqueous solution of choline hydroxide [Ch]OH as catalysts for executing Aza-Michael addition of N-heterocycles to α,β-unsaturated compounds at room temperature. The highlighting features of these catalysts include using low concentration of both catalysts along with [Ch]OH being low cost and biodegradable, [n-butyl Urotropinium]OH significantly enhancing the high substrate/catalyst ratio to obtain the desired products in high yield and purity in most cases. Further, both catalysts were recyclable and recoverable up to five cycles.
- Kumar, Sitanshu,Kaur, Amanpreet,Singh, Vasundhara
-
p. 193 - 201
(2019/01/24)
-
- TiCl2(OTf)-SiO2: A solid stable lewis acid catalyst for Michael addition of α-Aminophosphonates, Amines, Indoles and Pyrrole
-
TiCl2(OTf)-SiO2 is simply prepared by immobilization of TiCl3(OTf) on silica gel surface and introduced as a non-hygroscopic Lewis acid catalyst for C-N and C-C bond formation via Michael addition reaction. A variety of structurally diverse nitrogen nucleophiles including α-aminophosphonates, aliphatic and aromatic amines and imidazole were evaluated as Michael donors. Friedel–Crafts alkylation of indoles and pyrrole was also investigated through Michael addition reaction in the presence of TiCl2(OTf)-SiO2 as a catalyst. The reactions were conducted at room temperature or 60 °C under solvent-free conditions and the desired Michael adducts were obtained in high to excellent yields.
- Firouzabadi, Habib,Iranpoor, Naser,Farahi, Soghra
-
p. 317 - 323
(2018/02/06)
-
- Method for synthesizing 1-(3-aminopropyl)imidazole from imidazole
-
The invention discloses a method for synthesizing 1-(3-aminopropyl)imidazole from imidazole. The method comprises the following steps: a, adding 28-32 parts by weight of the imidazole, 55-65 parts byweight of acrylonitrile, and 0.9-1.1 parts by weight of ethyl acetate into a reaction kettle, rapidly raising the temperature to 42-44 DEG C under sealed conditions, and performing stirring continuously for 22-28min; and introducing a nitrogen gas for cooling until the temperature is -5 DEG C, adding dilute sulfuric acid to adjust the pH value to 2.2-2.4, and performing stirring for 10-20min for precipitating a crystal; b, washing the crystal with saturated salt water, performing vacuum drying, and performing cooling to normal temperature to obtain N-(2-cyanoethyl)imidazole and other steps. The preparation method provided by the invention is scientific and simple, strictly controls the formula ratio, and controls the reaction conditions, the raw materials are easy to obtain, the usage amount of the raw materials is small, the cost is low, and the prepared 1-(3-aminopropyl)imidazole has high purity, a high yield and stable performance, and is suitable for industrialized production.
- -
-
Paragraph 0031-0034; 0038-0041; 0045-0048
(2018/04/26)
-
- Ionic liquid catalytic amine with the α, β-unsaturated electron deficient receptor method
-
The invention relates to a method for catalyzing amines and alpha, beta-unsaturated electron-deficient acceptors by an ionic liquid. The method comprises the following steps: by taking the ionic liquid as a catalyst, carrying out a catalytic addition reaction on alpha, beta-unsaturated electron-deficient acceptors such as amines, acrylate and acrylonitrile at room temperature and at normal pressure, and carrying out column chromatography to obtain a corresponding addition product; magnetically stirring at room temperature without a solvent, after reaction, extracting the ionic liquid by water and ethyl acetate; carrying out column chromatography on an organic phase to obtain a product; and re-putting the filtrate with the water phase of the ionic liquid without vapor at high temperature in vacuum to react. Through verification, the product can be used as a catalytic reaction system which is repeatedly used for 6 times, and no remarkable reaction yield reduction is discovered. The method is simple to operate, high in yield, good in reusability of the catalytic reaction system and mild reaction condition and has a good industrialized prospect.
- -
-
Paragraph 0038-0039
(2017/02/09)
-
- CO2 capture by task specific ionic liquids (TSILs) and polymerized ionic liquids (PILs and AAPILs)
-
In the present study, new ionic liquids (ILs) such as task specific ionic liquids (TSILs), polymerized ionic liquids (PILs), and amino acid-based polymerized ionic liquids (AAPILs) were synthesized and their efficiency for capturing CO2 was stu
- Raja Shahrom, Maisara Shahrom,Wilfred, Cecilia Devi,Taha, Abobakr Khidir Ziyada
-
p. 306 - 312
(2016/04/05)
-
- Ultrasound assisted synthesis of imidazolium salts: An efficient way to ionic liquids
-
In this study a straightforward and efficient approach concerning synthesis of 1,3-diazole derivatives under ultrasound (US) irradiation as well as under conventional thermal heating (TH) is presented. N-alkylation under US irradiation may be considered environmentally friendly in terms of higher yields, smaller amounts of solvent used and an overall energy efficiency due to a substantial reduction of reaction times. A comparative study of ultrasound vs. conventional conditions has been performed. Overall, the use of US proved to be more efficient than TH. A possible explanation concerning the different behavior of imidazole and benzimidazole in the N1-alkylation reactions under US irradiation was proposed.
- Zbancioc, Gheorghita,Mangalagiu, Ionel I.,Moldoveanu, Costel
-
p. 376 - 384
(2015/02/19)
-
- Highly efficient and green chemical synthesis of imidazolyl alcohols and N-imidazolyl functionalized β-amino compounds using nanocrystalline ZSM-5 catalysts
-
A solvent free protocol is developed for the synthesis of imidazolyl alcohols and N-imidazolyl functionalized β-amino compounds. Imidazolyl alcohols were synthesized by the ring opening of epoxides with imidazoles and N-imidazolyl functionalized β-amino compounds were synthesized by the hydroamination reaction of imidazoles and activated olefins. These reactions were catalyzed by a variety of crystalline heterogeneous catalysts such as Al/Zr substituted nanocrystalline ZSM-5 (M-Nano-ZSM-5), conventional M-ZSM-5 (where M = Zr, Al), and Zr substituted amorphous mesoporous catalysts (Zr-SBA-15 and Zr-KIT-6). Among these catalysts, nanocrystalline Zr-Nano-ZSM-5 exhibited the highest activity and regioselectivity. Structure activity relationship is explained based on the catalytic activity, acidity measurements, reactivity of reactants (imidazoles/epoxides/methyl acrylate), competitive adsorption, nature, and type of catalysts. Zr-Nano-ZSM-5 exhibited exceptionally high catalytic activity compared to the catalysts reported in the literature for the synthesis of imidazolyl alcohols and other imidazole derivatives.
- Kore, Rajkumar,Satpati, Biswarup,Srivastava, Rajendra
-
-
- CO2/N2 triggered Switchable surfactants with imidazole group
-
In order to overcome the hydrolysis of 2-alkyl-1-hydroxyethyl imidazoline and its unsatisfactory emulsification-demulsification switchability to water-alkane, the long-chain N-alkylimidazole compounds were synthesized by n-octyl bromide, n-decyl bromide, n-dodecyl bromide, n-tetradecyl bromide and n-hexadecyl bromide with imidazole, respectively and characterized by MS, 1H NMR and FTIR. The long-chain N-alkylimidazole compounds can be reversibly transformed into charged surfactants by exposure to CO2. Surface tension values indicated that N-alkylimidazolium bicarbonates had excellent surface activity compared with corresponding conventional surfactants with a lower γ CMC. The surface behaviors of the five surfactants can be illustrated by A min. Five conductivity cycles by bubbling CO2 and N2 alternately indicated that these surfactants could be switched by CO2 reversibly and repeatedly. Emulsions were repeatedly stabilized for five cycles by N-alkylimidazolium bicarbonate and broken by bubbling N2 through the solutions to reverses the reaction, releasing CO2.
- Chai, Mingfeng,Zheng, Zhibo,Bao, Lei,Qiao, Weihong
-
p. 383 - 390
(2014/05/20)
-
- Polystyrene-supported CuI-imidazole complex catalyst for aza-Michael reaction of imidazoles with α,β-unsaturated compounds
-
The polystyrene-supported CuI-imidazole complex catalyst was prepared and characterized by IR spectroscopy, elemental analysis, SEM/TEM and TG/DSC. The complex catalyst was globular with the size of 400-500 nm and showed a good thermal stability at high temperature. The immobilized Cu metal in the complex catalyst was about 0.85 mmol/g. By using the catalyst, aza-Michael reaction of imidazoles to α,β-unsaturated compounds was performed with good yields in 4-8 h. The catalyst showed an excellent recycling efficiency over five cycles without distinct leaching of metal from the polymer support.
- Li, Lixia,Liu, Zuliang,Ling, Qilong,Xing, Xiaodong
-
experimental part
p. 178 - 184
(2012/03/09)
-
- Solvent-free aza-Markovnikov and aza-Michael additions promoted by a catalytic amount of imidazolide basic ionic liquids
-
A family of imidazolide ionic liquids were synthesized and characterized. These ionic liquids combined the virtues of strong basicity and relatively good thermal stability. Catalytic properties of these imidazolide ionic liquids were investigated and satisfactory yield was achieved when 2.0 mol % of [Bmim]Im was used as catalyst for aza-Markovnikov addition under solvent-free condition at room temperature in one hour. Experimental results show that a hydrogen bond is not formed between [Bmim]Im/imidazole and vinyl ester, and its existence is not necessary for the [Bmim]Im catalyzed aza-Markovnikov addition either. A possible mechanism for [Bmim]Im-catalyzed aza-Markovnikov addition was proposed. The use of imidazolide ionic liquids in aza-Michael addition was investigated as well.
- Chen, Xuewei,Li, Xuehui,Song, Hongbing,Qian, Yu,Wang, Furong
-
supporting information; experimental part
p. 3588 - 3591
(2011/07/29)
-
- Synthesis of N-cyanoalkyl-functionalized imidazolium nitrate and dicyanamide ionic liquids with a comparison of their thermal properties for energetic applications
-
The synthesis of 10 N-alkyl-N-cyanoalkyl-functionalized imidazolium (N-methyl- and N-butyl-N-((CH2)nCN)imidazolium; n = 1-4) nitrate and 11 N-alkyl-N-cyanoalkyl-functionalized imidazolium (N-methyl-N-((CH2)nCN)imidazolium; n = 1-6, N-(2-cyanoethyl)-N-((CH2)nCN)imidazolium; n = 1,3-6) dicyanamide salts was achieved via N-alkylation of substituted imidazoles with commercially available haloalkylnitriles followed by anion exchange. Based on their observed melting points, all dicyanamide salts and all but one nitrate salt (1-cyanomethyl-3-methylimidazolium nitrate) had melting points 100 °C, as did 13 of the 17 halide precursors also reported here. Differential scanning calorimetry data indicated that melting points decreased by increasing the N-alkyl or N-cyanoalkyl chain length or by exchanging with the dicyanamide anion, which produced the lowest melting points in comparison to analogous halide or nitrate salts. Thermogravimetric analyses indicated that thermal stability increased for longer N-cyanoalkyl substituent lengths and decreased significantly for nitrates and more so for dicyanamides bearing short-chain N-cyanoalkyl substituents (e.g., N-cyanomethyl, N-(1-cyanoethyl), and N-(2-cyanoethyl)) in comparison to halide precursors. Furthermore, for many of the N-cyanoalkyl-substituted salts (especially the dicyanamides), there was a significant production of thermally-stable char - presumably due to by-products formed from the reaction of either N-cyanoalkyl substituents, dicyanamide anion, or both, which resulted in thermally-stable polymers or cycles.
- Drab, David M.,Smiglak, Marcin,Shamshina, Julia L.,Kelley, Steven P.,Schneider, Stefan,Hawkins, Tommy W.,Rogers, Robin D.
-
experimental part
p. 1701 - 1717
(2011/10/02)
-
- Crown ether complex cation ionic liquids: Preparation and applications in organic reactions
-
A series of crown ether complex cation ionic liquids (CECILs) were designed, synthesised and characterised by NMR spectroscopy, HRMS, thermogravimetric differential thermal analysis (TG-DTA) and elemental analysis. Their applications in various organic reactions were investigated: [15-C-5Na][OH], [15-C-5Na][OAc], [18-C-6K][OH] and [18-C-6K][OAc] (15-C-5=[15]crown-5; 18-C-6=[18]crown-6) efficiently catalysed the Michael addition of alkenes and relevant nucleophiles; [18-C-6K][OH] and [15-C-5Na][OH] effectively catalysed the Henry reaction of nitromethane and aromatic aldehydes; [18-C-6K][OH] has excellent catalytic efficiency for Knoevenagel condensation of aromatic aldehydes and malononitrile; PdCl2/[18-C-6K] 3[PO4]/K2CO3 efficaciously catalysed the Heck reaction of olefins and aromatic halides; [18-C-6K][BrO3] can be used as both oxidant and solvent in the oxidation reaction of aromatic alcohols. The CECIL catalysts [15-C-5Na][OH] (Michael addition) and [18-C-6K][OH] (Henry reaction) can be recycled and reused several times without obvious loss of activity and their recovery is very simple.
- Song, Yingying,Jing, Huanwang,Li, Bo,Bai, Dongsheng
-
experimental part
p. 8731 - 8738
(2011/09/16)
-
- Effect of sulfonate-based anions on the physicochemical properties of 1-alkyl-3-propanenitrile imidazolium ionic liquids
-
In this paper, the physicochemical properties of a new series of ionic liquids (ILs) based on nitrile-functionalised imidazolium cations ([C 2CN Cnim]+) with sulfonate-based anions were studied. The ILs were prepared by re
- Ziyada, Abobakr Khidir,Bustam, Mohamad Azmi,Murugesan, Thanapalan,Wilfred, Cecilia Devi
-
experimental part
p. 1111 - 1116
(2011/07/08)
-
- Thermal stability of 1,3-disubstituted imidazolium tetrachloroferrates, magnetic ionic liquids
-
Thermal stability of synthesized magnetic liquids, tetrachloroferrates of 1,3-disubstitued derivatives of imidazolium, was examined. An effect of the cation structure on thermal stability of ionic liquids was considered and a mechanism of thermal destruction was suggested.
- Zhuravlev,Verolainen,Voronchikhina
-
experimental part
p. 1158 - 1164
(2011/11/30)
-
- Densities, viscosities, and refractive indices of 1-hexyl-3-propanenitrile imidazolium ionic liquids incorporated with sulfonate-based anions
-
A new series of nitrile-functionalized room-temperature ionic liquids (RTILs), incorporating different anions, namely, dioctylsulfosuccinate, dodecylsulfate, benzenesulfonate, sulfobenzoate, and triflouromethanesulfonate, have been prepared and characteri
- Ziyada, Abobakr K.,Bustam, M. Azmi,Wilfred, Cecilia D.,Murugesan, Thanapalan
-
experimental part
p. 2343 - 2348
(2011/12/21)
-
- Microwave-assisted ligand-free, base-free Heck reactions in a task-specific imidazolium ionic liquid
-
1-(2-cyanoethyl)-3-(2-hydroxyethyl)-1H-imidazol-3-ium tetrafluoroborate (IL-2) in presence of PdCl2 was found to be an efficient and reusable, ligand-free, base-free catalytic system for Heckcoupling of activated and deactivated iodo-and bromoarenes with different olefins. Under microwave irradiation, it exhibited good efficiency in terms of activity, selectivity and recyclability for six consecutive runs without significant loss of activity. ARKAT-USA, Inc.
- Dighe, Mahesh G.,Degani, Mariam S.
-
experimental part
p. 189 - 197
(2012/02/03)
-
- Mild and efficient procedure for michael addition of n-heterocycles to,-unsaturated compounds using anhydrous K3PO4 as catalyst
-
Imidazole, 1,2,4-triazole, indole, and benzotriazole undergo conjugate additions with,α,β-unsaturated carbonyl compounds in the presence of anhydrous potassium phosphate at ambient temperature to afford the corresponding Michael adducts in excellent yields.
- Hou, Xueling,Hemit, Helimay,Yong, Jianping,Nie, Lifei,Aisa, Haji Akber
-
experimental part
p. 973 - 979
(2010/05/18)
-
- An effective aza-michael addition of aromatic amines to electron-deficient alkenes in alkaline Al2O3
-
Aza-Michael addition of aromatic or aliphatic amines with various electron-deficient alkenes was performed using alkaline Al2O 3 as solid media at room temperature afforded the corresponding Michael addition products in good to excellent yields.The alkaline Al 2O3 can be easily recovered and reused.
- Ai, Xin,Wang, Xin,Liu, Jin-Ming,Ge, Ze-Mei,Cheng, Tie-Ming,Li, Run-Tao
-
experimental part
p. 5373 - 5377
(2010/08/06)
-
- Aza-michael addition of amines to α,β-unsaturated compounds using molecular iodine as catalyst
-
Aza-Michael adducts are obtained in very good yields by the conjugate addition of aliphatic amines to α,β-unsaturated compounds using molecular iodine as catalyst in dichloromethane at room temperature. Aromatic amines were found to be reactive under reflux in toluene.
- Borah, Kalyan Jyoti,Phukan, Mridula,Borah, Ruli
-
experimental part
p. 2830 - 2836
(2010/11/02)
-
- A general design platform for ionic liquid ions based on bridged multi-heterocycles with flexible symmetry and charge
-
A conceptual design platform for new ionic liquids with variable heterocycles, bridges, symmetry, and charge was developed using simple alkylation, click, and ionic liquid chemistries and demonstrated with 1-(2-(5-tetrazolidyl)ethyl)-3-(5-1H-tetrazolyl)methylimidazolium and its conversion into room-temperature ionic liquids as cation or as anion.
- Drab, David M.,Shamshina, Julia L.,Smiglak, Marcin,Hines, C. Corey,Cordes, David B.,Rogers, Robin D.
-
supporting information; experimental part
p. 3544 - 3546
(2010/08/07)
-
- Iodine-alumina catalyzed Aza- michael addition under solvent free conditions
-
An efficient aza-Michael addition of amines to a variety of activated olefins was carried out under solvent free conditions using iodine-alumina as a catalyst at room temperature or under microwave irradiation (in case of solid) in high yield. 2009 Bentham Science Publishers Ltd.
- Saikia, Monmi,Kakati, Dwipen,Joseph, Maria Stalin,Sarma, Jadab Chandra
-
experimental part
p. 654 - 658
(2010/06/15)
-
- Highly efficient Michael addition reaction of amines catalyzed by silica-supported aluminum chloride
-
Aliphatic and aromatic amines undergo smooth nucleophilic addition to α,β-unsaturated compounds in the presence of a catalytic amount of silica-supported aluminum chloride at 60°C and under solvent-free conditions to produce the corresponding β-amino compounds in excellent yields. This method is simple and convenient and works efficiently under mild conditions. This catalyst can used again without losing its activity three times. Copyright Taylor & Francis Group, LLC.
- Saidi, Mohammad R.,Pourshojaei, Yaghoub,Aryanasab, Fezzeh
-
experimental part
p. 1109 - 1119
(2009/09/08)
-
- Triethylammonium acetate (TEAA): A recyclable inexpensive ionic liquid promotes the chemoselective aza- and thia-Michael reactions
-
A new, highly efficient, inexpensive, recyclable, mild, convenient, and green protocol for chemoselective aza/thia-Michael addition reactions of amines/thiols to α,β-unsaturated compounds using triethylammonium acetate (TEAA) ionic liquid was developed. The catalyst can be recycled ten times and obviate the need for toxic and expensive catalysts.
- Verma, Akhilesh K.,Attri, Pankaj,Chopra, Varun,Tiwari, Rakesh K.,Chandra, Ramesh
-
experimental part
p. 1041 - 1047
(2009/11/30)
-
- Vanadyl(IV) acetate: An efficient, reusable heterogenous catalyst for Aza-Michael reaction under solvent-free conditions
-
Vanadyl(IV) acetate [VO(OAc)2] efficiently catalyzes the conjugate addition of aliphatic, aromatic amines to α,β-unsaturated carbonyl compounds in solvent-free media at room temperature to afford corresponding amino compounds in good to excellent yields. The catalyst can be recovered and reused for further cycles. Copyright Taylor & Francis Group, LLC.
- Trivedi, Rajiv,Lalitha,Roy, Sarabindu
-
p. 3556 - 3566
(2008/12/23)
-
- Synthesis of 4-substituted 2-carenes in novel imidazolinium ionic liquids
-
4-Acetyl-, 4-acetoxymethyl-, and 4-hydroxymethyl-2-carenes were synthesized using novel ionic liquids.
- MacAev,Gavrilov,Muntyanu,Styngach,Vlad,Bets,Pogrebnoi,Barba
-
p. 136 - 139
(2008/03/12)
-
- A fast and highly efficient protocol for Michael addition of N-heterocycles to α,β-unsaturated compound using basic ionic liquid [bmIm]OH as catalyst and green solvent
-
A fast and green protocol for the Michael addition of N-heterocycles to α,β-unsaturated compounds at room temperature was developed using a basic ionic liquid, 1-methyl-3-butylimidazolium hydroxide, [bmIm]OH, as a catalyst and a reaction medium. The react
- Xu, Jian-Ming,Qian, Chao,Liu, Bo-Kai,Wu, Qi,Lin, Xian-Fu
-
p. 986 - 990
(2007/10/03)
-
- Promiscuous acylase-catalyzed aza-Michael additions of aromatic N-heterocycles in organic solvent
-
A novel and efficient enzymatic promiscuous protocol for aza-Michael addition of aromatic N-heterocycles to α,β-unsaturated compounds has been described. The reactions were catalyzed by promiscuous zinc-active-site acylase in organic solvent at 50 °C. The strategy works with a broad range of N-heterocycles to afford the corresponding Michael adduct with good yields in several hours (0.5-6 h). This catalytic promiscuity is the first example of metal-active-site enzyme-catalyzed aza-Michael addition for aromatic N-heterocycles.
- Qian, Chao,Xu, Jian-Ming,Wu, Qi,Lv, De-Shui,Lin, Xian-Fu
-
p. 6100 - 6104
(2008/03/12)
-
- Cellulose-supported copper(0) catalyst for aza-Michael addition
-
Cellulose-supported copper(0) efficiently catalyzes the aza-Michael reaction of N-nucleophiles, such as amines and imidazoles with α,β-unsaturated compounds to produce the corresponding β-amino compounds and N-substituted imidazoles in excellent yields. The reactions are facile and the recovered catalyst is used for several cycles with consistent activity. Georg Thieme Verlag Stuttgart.
- Reddy, K. Rajender,Kumar, Nadakudity S.
-
p. 2246 - 2250
(2007/10/03)
-
- Highly efficient aza-Michael reactions of aromatic amines and N-heterocycles catalyzed by a basic ionic liquid under solvent-free conditions
-
A task-specific basic ionic liquid, [Bmim]OH, has been introduced as a catalyst for the aza-Michael addition of aromatic amines and N-heterocycles to cyclic or acyclic ketones under neat conditions. The catalyst can be recycled for subsequent reactions without any appreciable loss of efficiency.
- Yang, Lei,Xu, Li-Wen,Zhou, Wei,Li, Lyi,Xia, Chun-Gu
-
p. 7723 - 7726
(2007/10/03)
-
- 1,2,3-Benzothiadiazole derivatives
-
Novel 1,2,3-benzothiadiazole derivatives of the formula STR1 in which Het has the meanings set forth in the specification, and addition products thereof with an acid or metal salt are very effective for the control of undesired microorganisms. Novel intermediates of the formulae STR2 in which Het1 and R5 have the meanings given in the specification.
- -
-
-
- Chloropyridylcarbonyl derivatives
-
Novel chloropyridylcarbonyl derivatives of the formula STR1 in which Het is STR2 n is 1 or 2, R1 is hydrogen, optionally substituted C1-6 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C3-6 alkynyl, optionally substituted phenyl or optionally substituted pyrimidinyl, and R2 and R3, independently of each other, are hydrogen or C1-4 alkyl, and acid addition salts and metal salt complexes thereof, are outstandingly active as microbicides.
- -
-
-
- Condensed thiazole derivative, production process thereof and pharmaceutical composition thereof
-
Condensed thiazole derivatives useful as 5-HT3 receptor agonists are provided and can be represented by the following formula (I) or a pharmaceutically acceptable salt thereof, a process for the production thereof and a pharmaceutical composition thereof: STR1 wherein R, A, L1, L2, L, and R1 -R6 are defined herein and Im represents a group of the formula: STR2
- -
-
-
- meso (Methine) Functionalization of Octa-alkylporphyrins
-
meso-Acetoxymethylocta-alkylporphyrins react with a variety of nucleophiles such as alcohols (to give the corresponding alkoxymethylporphyrins), amines (yielding aminomethylporphyrins), and Grignard reagents (to give meso-alkylporphyrins).Treatment of the meso-acetoxymethylporphyrins with thiol reagents accomplishes reduction to give the meso-methylporphyrin rather than the sulphide.Making use of these meso-functionalization reactions, potential cytochrome P450 models and a model for the tense form of hemoglobin are synthesized.
- Smith, Kevin M.,Bisset, Graham M. F.
-
p. 2625 - 2630
(2007/10/02)
-
