2463-16-3Relevant articles and documents
Production of Copolyester Monomers from Plant-Based Acrylate and Acetaldehyde
Yuan, Lin,Hu, Yancheng,Zhao, Zhitong,Li, Guangyi,Wang, Aiqin,Cong, Yu,Wang, Feng,Zhang, Tao,Li, Ning
supporting information, (2021/12/14)
PCTA is an important copolyester that has been widely used in our daily necessities. Currently, its monomers are industrially produced from petroleum-derived xylene. To reduce the reliance on fossil energy, we herein disclose an alternative route to acces
Oxidative Esterification of Aldehydes and Alcohols Catalyzed by Camphor-Based Imidazolium Salts
Bian, Tiancen,Feng, Li,Li, Danfeng,Huang, Jiaxin,Zhao, Yuxun,Xu, Xu,Yang, Yiqin,Wang, Shifa
, p. 1812 - 1820 (2020/01/11)
Abstract: Sixteen new camphor-based imidazolium salts have been synthesized with renewable camphorsulfonic acid as the starting material. The chemical shifts of the characteristic proton of C2 on the imidazolium ring (N?C=N) were discussed thoroughly and all of these imidazolium salts exhibit good thermal stability. Furthermore, the excellent catalytic performance of the synthesized imidazolium salts were observed in the oxidative esterification between aromatic or aliphatic aldehydes containing electron-withdrawing or electron-donating groups on aromatic ring and primary or secondary alcohol by air as the sole oxidant. Graphic Abstract: [Figure not available: see fulltext.].
Camphoryl imidazole type ionic liquid and preparation method and application thereof
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Paragraph 0060; 0072, (2019/10/05)
The invention discloses a camphoryl imidazole type ionic liquid and a preparation method and application thereof. According to the preparation method, a derivative camphorsulfonic acid of a natural renewable resource camphor is taken as a raw material to prepare 10-iodocamphor; then the 10-iodocamphor and aryl imidazole are subjected to a quaterisation reaction to prepare camphoryl imidazole iodide; then the camphoryl imidazole iodide and sodium hexafluorophosphate, sodium tetrafluoroborate, bis(trifluorosulfonimide)lithium and the like are subjected to ion exchange to prepare camphoryl imidazole hexafluorophosphate, camphoryl imidazole tetrafluoroborate, camphoryl imidazole bis(trifluorosulfonimide)salt and other ionic liquids. The camphoryl imidazole type ionic liquid shows good catalytic activity for an oxidation esterification reaction of aldehyde-alcohol, has the advantages of short reaction time, good reaction selectivity and high product yield, and has a good application prospect.
Application of Continuous Flow-Flash Chemistry to Scale-up Synthesis of 5-Cyano-2-formylbenzoic Acid
Seto, Masaki,Masada, Shinichi,Usutani, Hirotsugu,Cork, David G.,Fukuda, Koichiro,Kawamoto, Tetsuji
, p. 1420 - 1428 (2019/07/03)
Efficient scale-up synthesis of 5-cyano-2-formylbenzoic acid or its cyclic isomer 6-cyano-3-hydroxy-2-benzofuran-1(3H)-one (1) as a key intermediate for various biologically important compounds has been achieved from isopropyl 2-bromo-5-cyanobenzoate (8c) by means of continuous flow-flash chemistry using flow microreactors. It was found that Br/Li exchange reaction of 8c, bearing both a carboisopropoxy group and a cyano group, with BuLi took place within 0.1 s at -50 °C, and the resulting highly reactive aryllithium intermediate underwent formylation with DMF to afford 1, which is extremely difficult to achieve by a conventional batch process. Optimization of the continuous flow-flash reaction conditions and modification of the reaction system brought about the production of 237 g of 1 from 897 g of 8c in 270 min, without purification by column chromatography. The results suggest that phthalaldehydic acid derivatives bearing electrophilic group(s) can be synthesized conveniently from the corresponding 2-bromobenzoic acid esters by means of flow-flash chemistry using flow microreactors.
Preparing method of aromatic nitrile or alkenyl nitrile compound
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Paragraph 0130-0132; 0166-0168; 0232-0233, (2019/10/01)
The invention discloses a preparing method of an aromatic nitrile or alkenyl nitrile compound. The preparing method comprises the following step that under protection of inert gas, an aryl or heteroaryl sulphonate compound shown in a formula II or an alkenyl sulphonate compound shown in a formula IV and a cyanation reagent are subjected to a cross-coupling reaction as is shown below in a solvent under the condition of the presence of a nickel complex, metal zinc and an additive to obtain the aromatic nitrile or alkenyl nitrile compound, wherein 4-dimethylamiopryidine (DMAP) is adopted as the additive, and zinc cyanide is adopted as the cyanation reagent. By means of the preparing method, cyanation of aryl sulphonate, heteroaryl sulphonate or alkenyl sulphonate can be simply and efficientlyachieved with a cheap catalysis system; moreover, the functional group compatibility and substrate universality are good, and a better application prospect and higher using value are provided for achieving industrial synthesis of the aromatic nitrile or alkenyl nitrile compound.
A Triazolotriazine-Based Dual GSK-3β/CK-1δ Ligand as a Potential Neuroprotective Agent Presenting Two Different Mechanisms of Enzymatic Inhibition
Redenti, Sara,Marcovich, Irene,De Vita, Teresa,Pérez, Concepción,De Zorzi, Rita,Demitri, Nicola,Perez, Daniel I.,Bottegoni, Giovanni,Bisignano, Paola,Bissaro, Maicol,Moro, Stefano,Martinez, Ana,Storici, Paola,Spalluto, Giampiero,Cavalli, Andrea,Federico, Stephanie
supporting information, p. 310 - 314 (2019/01/24)
Glycogen synthase kinase 3β (GSK-3β) and casein kinase 1δ (CK-1δ) are emerging targets for the treatment of neuroinflammatory disorders, including Parkinson's disease. An inhibitor able to target these two kinases was developed by docking-based design. Compound 12, 3-(7-amino-5-(cyclohexylamino)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-2-yl)-2-cyanoacrylamide, showed combined inhibitory activity against GSK-3β and CK-1δ [IC50(GSK-3β)=0.17 μm; IC50(CK-1δ)=0.68 μm]. In particular, classical ATP competition was observed against CK-1δ, and a co-crystal of compound 12 inside GSK-3β confirmed a covalent interaction between the cyanoacrylamide warhead and Cys199, which could help in the development of more potent covalent inhibitors of GSK-3β. Preliminary studies on in vitro models of Parkinson's disease revealed that compound 12 is not cytotoxic and shows neuroprotective activity. These results encourage further investigations to validate GSK-3β/CK-1δ inhibition as a possible new strategy to treat neuroinflammatory/degenerative diseases.
Nickel-Catalyzed Cyanation of Phenol Derivatives with Zn(CN)2 Involving C-O Bond Cleavage
Gan, Yi,Wang, Gaonan,Xie, Xin,Liu, Yuanhong
, p. 14036 - 14048 (2018/11/03)
An efficient nickel-catalyzed cyanation of aryl sulfonates, fluorosulfonates, and sulfamates with Zn(CN)2 was developed, which provides a facile access to the nitrile products in generally good to excellent yields. The reaction is accomplished by using NiII complex as the precatalyst and DMAP as the additive. The method also displays wide functional group compatibility; for example, keto, methoxy, N,N-dimethylamino, cyano, ester, and pyridyl groups are well-tolerated during the reaction process.
Oxidative Esterification of Aromatic Aldehydes Using Polymer-Supported Green Bromine
Sridhar,Swarnalakshmi,Selvaraj
, p. 1344 - 1348 (2016/06/01)
A facile one-pot green chemical conversion of aromatic aldehydes to alkyl esters is described using polymer-supported bromine chloride resin in the presence of potassium carbonate at room temperature. This eco-friendly methodology with simple workup procedure and recovery and recyclability of the resin makes the transformation simple and efficient.
One-pot synthesis of amidoxime via Pd-catalyzed cyanation and amidoximation
Yang, Chu-Ting,Han, Jun,Liu, Jun,Gu, Mei,Li, Yi,Wen, Jun,Yu, Hai-Zhu,Hu, Sheng,Wang, Xiaolin
supporting information, p. 2541 - 2545 (2015/04/14)
A novel "one-pot" reaction was developed for the synthesis of aryl or heteroaryl-substituted amidoxime compounds containing various functional groups. Fluorescence titration experiments coupled with theoretical analysis revealed that the steric hindrance and electronic effects of substituents influence the binding ability of the amidoxime compounds to uranyl ions. This journal is
New in situ trapping metalations of functionalized arenes and heteroarenes with TMPLi in the presence of ZnCl2 and other metal salts
Frischmuth, Annette,Fernandez, Maitane,Barl, Nadja M.,Achrainer, Florian,Zipse, Hendrik,Berionni, Guillaume,Mayr, Herbert,Karaghiosoff, Konstantin,Knochel, Paul
supporting information, p. 7928 - 7932 (2014/08/05)
The addition of TMPLi to a mixture of an aromatic or heteroaromatic substrate with a metal salt such as MgCl2, ZnCl2, or CuCN at -78 °C first leads to lithiation of the arene followed by transmetalation with the metal salt to afford functionalized organometallic compounds of Mg, Zn, or Cu. This in situ trapping method allows an expedited metalation (-78 °C, 5 min) of a range of sensitive pyridines (bearing a nitro, ester, or cyano group) and allows the preparation of kinetic regioisomers of functionalized aromatic compounds or heterocycles not otherwise available by standard metalating agents, such as TMPMgCl·LiCl or TMPZnCl·LiCl. Fast, faster, the fastest: Aromatic and heterocyclic substrates, when treated with TMPLi (TMP=2,2,6,6-tetramethylpiperidyl), undergo a kinetic lithiation and then a transmetalation with a metal salt such as MgCl2, ZnCl 2, or CuCN. This allows an expedited metalation of sensitive pyridines bearing a nitro, ester, or cyano group and allows the preparation of kinetic regioisomers of functionalized aromatic compounds or heterocycles.
