4254-18-6Relevant articles and documents
Diastereoselective construction of cyclopent-2-enone-4-ols from aldehydes and 1,2-allenones catalyzed by N-heterocyclic carbene
Ma, Dengke,Fu, Chunling,Ma, Shengming
, p. 14426 - 14429 (2016)
Cyclopent-2-enone-4-ols have been prepared highly diastereoselectively from readily available aromatic aldehydes and 1,2-allenones catalyzed by N-heterocyclic carbene. Mechanistic studies showed that there are four possible pathways.
Functionalizing tetraphenylpyrazine with perylene diimides (PDIs) as high-performance nonfullerene acceptors
Li, Gang,Yang, Shufan,Liu, Tao,Li, Jiewei,Yang, Wenbin,Luo, Zhenghui,Yan, Cenqi,Li, Dandan,Wang, Xinyu,Cui, Guanwei,Yang, Tao,Xu, Liang,Zhan, Shun-Ze,Huo, Lijun,Yan, He,Tang, Bo
, p. 14563 - 14570 (2019)
Perylene diimide (PDI)-based small molecular acceptors with a three-dimensional structure are thought to be essential for efficient photocurrent generation and high power conversion efficiencies (PCEs). Herein, a couple of new perylene diimide acceptors (
Insights into the synthesis of hexaaminobenzene hydrochloride: An entry to hexaazatriphenylenes
Comba, María Betina,Libonatti, Bernardo,Mangione, María Inés,Spanevello, Rolando A.,Vázquez, Darián
, (2022/01/22)
Polycyclic N-heteroaromatic systems and particularly, the dipyrazino[2,3-f:2′,3′-h]quinoxaline also known as 1,4,5,8,9,12-hexaazatriphenylene (HAT) displays very useful optoelectronic properties. Its synthesis through condensation of functionalized 1,2-diketones and hexaaminobenzene is often applied on laboratory scale. Hexaaminobenzene could be prepared from 4-nitroaniline but, despite its many applications, the experimental protocol is not trivial and should by carefully controlled in each step. In this work, we presented an efficient and reproducible 4 steps synthesis of hexaaminobenzene hydrochloride and a comprehensive analysis of reactions conditions and products formed in all synthetic steps. As evidence, this aromatic polyamine was effectively condensed with 1,2-di(4-bromophenyl)-1,2-ethanedione affording a synthetically versatile HAT derivative for the application in the design of organic materials.
Organocatalytic Synthesis of Substituted Vinylene Carbonates
Onida, Killian,Haddleton, Alice J.,Norsic, Sébastien,Boisson, Christophe,D'Agosto, Franck,Duguet, Nicolas
supporting information, p. 5129 - 5137 (2021/09/18)
The organocatalytic synthesis of substituted vinylene carbonates from benzoins and acyloins was studied using diphenyl carbonate as a carbonyl source. A range of N-Heterocyclic Carbene (NHC) precursors were screened and it was found that imidazolium salts were the most active for this transformation. The reaction occurs at 90 °C under solvent-free conditions. A wide range of substituted vinylene carbonates (symmetrical and unsymmetrical, aromatic or aliphatic), including some derived from natural products, were prepared with 20–99% isolated yields (24 examples). The reaction was also developed using thermomorphic polyethylene-supported organocatalysts as recoverable and recyclable species. The use of such species facilitates the workup and allows the synthesis of vinylene carbonates on the preparative scale (>30 g after 5 runs). (Figure presented.).
ORGANIC COMPOUNDS AND ORGANIC LIGHT EMITTING DISPLAY DEVICE USING THE SAME
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Paragraph 0131; 0132, (2021/07/02)
The present disclosure relates to an organic compound and an organic light emitting display device using the same wherein the organic compound is represented by Chemical Formula 1 and a display device using the organic compound. The organic compound represented by Chemical Formula 1 has excellent electron transport properties and durability and is used for an electron transport layer of an organic light emitting element, thereby lowering a driving voltage and improving the luminous efficiency and lifetime. (In the above Chemical Formula 1, at least two of X1, X2 and X3 are N, Y1 and Y2 are each independently a substituted or unsubstituted phenylene group or a single bond, at least one of Ar1 and Ar2 is selected from a substituted or unsubstituted triazine group, a functional group represented by Chemical Formula 2 and a functional group represented by Chemical Formula 3.)
Synthesis and in vitro anticancer activities of selenium N-heterocyclic carbene compounds
Huang, Sheng,Sheng, Xinyu,Bian, Mianli,Yang, Zhibin,Lu, Yunlong,Liu, Wukun
, p. 435 - 444 (2021/07/14)
Fourteen novel selenium N-heterocyclic carbene (Se-NHC) compounds derived from 4,5-diarylimidazole were designed, synthesized, and evaluated as antiproliferative agents. Most of them were more effective toward A2780 ovarian cancer cells than HepG2 hepatocellular carcinoma cells. Among them, the most active compound 2b was about fourfold more active than the positive control ebselen against A2780 cells. In addition, this compound displayed twofold higher cytotoxicity to A2780 cells than to IOSE80 normal ovarian epithelial cells. Further studies revealed that 2b could induce reactive oxygen species production, damage mitochondrial membrane potential, block the cells in the G0/G1 phase, and finally promote A2780 cell apoptosis.
Application of N-heterocyclic carbene selenium-gold compound in preparation of carbapenem-resistant acinetobacter baumannii drug
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Paragraph 0024; 0029-0032, (2021/07/21)
The invention discloses application of an N-heterocyclic carbene selenium-gold compound in preparation of a novel antibacterial drug resistant to carbapenem acinetobacter baumannii infection, and belongs to the technical field of drug preparation. According to the N-heterocyclic carbene selenium-gold compound, selenium-containing imidazole N-heterocyclic carbene selenium is used for replacing a thiosaccharide ligand in a gold nofen structure; the reaction activity of Au-Se in the N-heterocyclic carbene selenium-gold compound is higher than that of an Au-S bond, so that the Au-S bond in a Jinnofen structure can be prevented from being easily damaged by reducing mercaptan to a certain extent; and toxic and side effects are caused by metabolism before reaching a target spot. In-vitro antibacterial activity shows that IC50 of the compounds H7 and H8 in inhibition of carbapenem-resistant acinetobacter baumannii is 3.34 mu M and 4.67 mu M, MIC of the same are both 10 mu M, and MBC of the same are both 20 mu M. The animal in-vivo administration also shows a good anti-drug-resistant bacterium effect, which proves that the compound can significantly prolong the survival time of mice infected by drug-resistant bacteria, and has important practical application value.
Zinc salt-catalyzed reduction of α-aryl imino esters, diketones and phenylacetylenes with water as hydrogen source
Shen, Guoli,Liu, Haojie,Chen, Jingchao,He, Zhenxiu,Zhou, Yongyun,Wang, Lin,Luo, Yang,Su, Zhimin,Fan, Baomin
supporting information, p. 3601 - 3610 (2021/05/04)
The zinc salt-catalyzed reduction of α-aryl imino esters, diketones and phenylacetylenes with water as hydrogen source and zinc as reductant was successfully conducted. The presented method provides a low-cost, environmentally friendly and practical preparation of α-aryl amino esters, α-hydroxyketones and phenylethylenes. By using D2O as deuterium source, the corresponding products were obtained in high efficiency with excellent deuterium incorporation rate, which gives a cheap and safe tool for access to valuable deuterium-labelled compounds. This journal is
Preparation and Application of Silica Films Supported Imidazolium-Based Ionic Liquid as Efficient and Recyclable Catalysts for Benzoin Condensations
Qian, Cunwei,Yao, Changsheng,Yang, Liujun,Yang, Bo,Liu, Shuchun,Liu, Zongtang
, p. 1389 - 1396 (2019/11/21)
Abstract: Two silica films -immobilized imidazolium-based ionic liquids (TMICl @silica films) were prepared, characterized and utilized as efficient catalysts for the benzoin reaction. Combined characterization results from FT-IR, elemental analysis, N2 adsorption–desorption isotherms and SEM, suggested that the imidazolium-based ionic liquids were successfully immobilized on the silica films. Moreover, the catalytic performance tests demonstrated that silica films immobilized imidazolium-based ionic liquids (ILs) exhibited excellent activity for the benzoin reactions of aromatic aldehydes. The influence of catalyst concentration, temperature and reaction duration on the catalytic activity were investigated by employing 0.7TMICl @silica film(catalyst C) as the catalyst. The results also showed that the benzoin condensations of aromatic aldehydes could give desired products with satisfactory yields under the optimized conditions. Additionally, the catalyst can be effortlessly separated by filtration and reused more than five times without significant loss of activity. Graphic Abstract: [Figure not available: see fulltext.]
Pendant Alkoxy Groups on N-Aryl Substitutions Drive the Efficiency of Imidazolylidene Catalysts for Homoenolate Annulation from Enal and Aldehyde
Kyan, Ryuji,Mase, Nobuyuki,Narumi, Tetsuo,Sato, Kohei
supporting information, p. 19031 - 19036 (2020/08/25)
Hydrogen-transfer in the tetrahedral intermediate generated from an imidazolylidene catalyst and α,β-unsaturated aldehyde forms a conjugated Breslow intermediate. This is a critical step affecting the efficiency of the NHC-catalyzed γ-butyrolactone formation via homoenolate addition to aryl aldehydes. A novel type of imidazolylidene catalyst with pendant alkoxy groups on the ortho-N-aryl groups is described. Catalyst of this sort facilitates the formation of the conjugated Breslow intermediate. Studies of the rate constants for homoenolate annulation affording γ-butyrolactones, reveal that introduction of the oxygen atoms in the appropriate position of the N-aryl substituents can increase the efficiency of imidazolylidene catalysts. Structural and mechanistic studies revealed that pendant alkoxy groups can be located close to the proton of the tetrahedral intermediate, thereby facilitating the proton transfer.
