16681-65-5Relevant articles and documents
Intermolecular C?C Coupling between 1-Methyl-1,2,3-Triazole and 2,2′-Bipyridine or 1,10-Phenanthroline in MoII Complexes
Fombona, Sergio,Pérez, Julio,Díaz, Jesús,Riera, Lucía
, p. 17870 - 17873 (2017)
Unsupported 1-methyl-1,2,3-triazole has been coordinated to {Mo(η3-methallyl)(CO)2(N-N)} (N-N=2,2′-bipyridine, bipy; or 1,10-phenanthroline, phen) fragments, yielding cationic complexes that can be regarded as metalated triazolium salts. Their reactivity towards a strong base led to the deprotonation of the C5?H group of the triazole moiety, followed by an intermolecular nucleophilic attack to the ortho CH group of a bipy or phen ligand affording cyclic, bimetallic dearomatized C?C coupling products. The reaction of the neutral bipy derivative with an acid led to the formation of dihydropyridyl units by protonation of a CH group of the dearomatized rings, the dimeric nature of complexes being mantained upon protonation.
Dissolving cellulose in 1,2,3-triazolium-and imidazolium-based ionic liquids with aromatic anions
Brehm, Martin,Kressler, J?rg,Pulst, Martin,Radicke, Julian,Sebastiani, Daniel,Shaabani, Farzaneh
, (2020)
We present 1,2,3-triazolium- and imidazolium-based ionic liquids (ILs) with aromatic anions as a new class of cellulose solvents. The two anions in our study, benzoate and salicylate, possess a lower basicity when compared to acetate and therefore should lead to a lower amount of N-heterocyclic carbenes (NHCs) in the ILs. We characterize their physicochemical properties and find that all of them are liquids at room temperature. By applying force field molecular dynamics (MD) simulations, we investigate the structure and dynamics of the liquids and find strong and long-lived hydrogen bonds, as well as significant π–π stacking between the aromatic anion and cation. Our ILs dissolve up to 8.5 wt.-percent cellulose. Via NMR spectroscopy of the solution, we rule out chain degradation or derivatization, even after several weeks at elevated temperature. Based on our MD simulations, we estimate the enthalpy of solvation and derive a simple model for semi-quantitative prediction of cellulose solubility in ILs. With the help of Sankey diagrams, we illustrate the hydrogen bond network topology of the solutions, which is characterized by competing hydrogen bond donors and acceptors. The hydrogen bonds between cellulose and the anions possess average lifetimes in the nanosecond range, which is longer than found in common pure ILs.
Influence of the counteranion on the ability of 1-dodecyl-3-methyltriazolium ionic liquids to form mesophases
Stappert, Kathrin,ünal, Derya,Spielberg, Eike T.,Mudring, Anja-Verena
, p. 752 - 758 (2015)
The influence of the counteranion on the ability of the mesogenic cation 1-methyl-3-dodecyl-triazolium to form mesophases is explored. To that avail, salts of the cation with anions of different size, shape, and hydrogen bonding capability such as Cl-, Br-, I-, I3-, PF6-, and Tf2N- [bis(trifluorosulfonyl)amide] were synthesized and characterized. The crystal structures of the bromide, the iodide, and the triiodide reveal that the cations form bilayers with cations oriented in opposite directions featuring interdigitated alkyl tails. Within the layers, the cations are separated by anions. The rod-shaped triiodide anion forces the triazolium cation to align with it in this crystal structure but due to its space requirement reduces the alkyl chain interdigitation which prevents the formation of a mesophase. Rather the compound transforms directly from a crystalline solid to an (ionic) liquid like the analogous bis(trifluorosulfonyl)amide. In contrast, the simple halides and the hexafluorophosphate form liquid crystalline phases. Their clearing points shift with increasing anion radius to lower temperatures.
Ready Access to Anhydrous Anionic Lanthanide Acetates by Using Imidazolium Acetate Ionic Liquids as the Reaction Medium
Bousrez, Guillaume,Renier, Olivier,Kelley, Steven P.,Adranno, Brando,Tahavori, Elnaz,Titi, Hatem M.,Smetana, Volodymyr,Tang, Si-Fu,Mudring, Anja-Verena,Rogers, Robin D.
supporting information, p. 13181 - 13189 (2021/08/16)
Access to lanthanide acetate coordination compounds is challenged by the tendency of lanthanides to coordinate water and the plethora of acetate coordination modes. A straightforward, reproducible synthetic procedure by treating lanthanide chloride hydrates with defined ratios of the ionic liquid (IL) 1-ethyl-3-methylimidazolium acetate ([C2mim][OAc]) has been developed. This reaction pathway leads to two isostructural crystalline anhydrous coordination complexes, the polymeric [C2mim]n[{Ln2(OAc)7}n] and the dimeric [C2mim]2[Ln2(OAc)8], based on the ion size and the ratio of IL used. A reaction with an IL : Ln-salt ratio of 5 : 1, where Ln=Nd, Sm, and Gd, led exclusively to the polymer, whilst for the heaviest lanthanides (Dy?Lu) the dimer was observed. Reaction with Eu and Tb resulted in a mixture of both polymeric and dimeric forms. When the amount of IL and/or the size of the cation was increased, the reaction led to only the dimeric compound for all the lanthanide series. Crystallographic analyses of the resulting salts revealed three different types of metal-acetate coordination modes where η2μκ2 is the most represented in both structure types.
TETRAHYDRONAPHTHYRIDINE DERIVATIVES AS mGluR2-NEGATIVE ALLOSTERIC MODULATORS, COMPOSITIONS, AND THEIR USE
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Page/Page column 51, (2016/03/22)
Provided are quinoline carboxamide and quinoline carbonitrile compounds of formula (I) or a pharmaceutically acceptable salt thereof, wherein R 1, R 2, L, X 1, X 2, and X 3, are as defined herein. The compounds of the invention, and pharmaceutically acceptable salts thereof, and pharmaceutical compositions comprising them, are useful as non-competitive mGluR2 antagonists, or mGluR2 negative allosteric modulators (NAMs), and may be useful in methods of treating a person in need thereof for diseases or disorders in which the mGluR2-NAM receptor plays a causative role, such as Alzheimer's disease, cognitive impairment, schizophrenia and other mood disorders, pain disorders and sleep disorders.
HETEROCYCLIC COMPOUNDS AS PESTICIDES
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, (2015/09/23)
The present application relates to the use of heterocyclic compounds for controlling animal pests including arthropods, insects and nematodes, to novel heterocyclic compounds, to processes for their preparation and to intermediates for preparing the heterocyclic compounds.
METHOD OF CONTROLLING LACTATE PRODUCTION WITH PIPERDINE-DIONE DERIVATIVES
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Page/Page column 102, (2015/11/10)
The invention provides novel compounds having the general formula: and tautomers and pharmaceutically acceptable salts thereof, wherein A1, A2, A3, A4, R1, R4, R5, R6, R7 and R8 are as defined herein, compositions including the compounds and methods of using the compounds.
PIPERIDINE-DIONE DERIVATIVES
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Page/Page column 115, (2015/11/10)
The invention provides novel compounds having the general formula (I) and tautomers and pharmaceutically acceptable salts thereof, wherein A1, A2, A3, A4, R1, R4, R5, R6, R7 and R8 are as defined herein, compositions including the compounds and methods of using the compounds.
Discovery and Optimization of Selective Nav1.8 Modulator Series That Demonstrate Efficacy in Preclinical Models of Pain
Bagal, Sharan K.,Bungay, Peter J.,Denton, Stephen M.,Gibson, Karl R.,Glossop, Melanie S.,Hay, Tanya L.,Kemp, Mark I.,Lane, Charlotte A. L.,Lewis, Mark L.,Maw, Graham N.,Million, William A.,Payne, C. Elizabeth,Poinsard, Cedric,Rawson, David J.,Stammen, Blanda L.,Stevens, Edward B.,Thompson, Lisa R.
supporting information, p. 650 - 654 (2015/06/30)
Voltage-gated sodium channels, in particular Nav1.8, can be targeted for the treatment of neuropathic and inflammatory pain. Herein, we described the optimization of Nav1.8 modulator series to deliver subtype selective, state, and use-dependent chemical matter that is efficacious in preclinical models of neuropathic and inflammatory pain. (Chemical Presented).
Water-soluble NHC-Cu catalysts: Applications in click chemistry, bioconjugation and mechanistic analysis
Daz Velzquez, Heriberto,Ruiz Garca, Yara,Vandichel, Matthias,Madder, Annemieke,Verpoort, Francis
supporting information, p. 9350 - 9356 (2014/12/11)
Copper(i)-catalyzed 1,3-dipolar cycloaddition of azides and terminal alkynes (CuAAC), better known as "click" reaction, has triggered the use of 1,2,3-triazoles in bioconjugation, drug discovery, materials science and combinatorial chemistry. Here we report a new series of water-soluble catalysts based on N-heterocyclic carbene (NHC)-Cu complexes which are additionally functionalized with a sulfonate group. The complexes show superior activity towards CuAAC reactions and display a high versatility, enabling the production of triazoles with different substitution patterns. Additionally, successful application of these complexes in bioconjugation using unprotected peptides acting as DNA binding domains was achieved for the first time. Mechanistic insight into the reaction mechanism is obtained by means of state-of-the-art first principles calculations.
