4254-20-0Relevant articles and documents
Synthesis, cytotoxic and antibacterial studies of p-benzyl-substituted NHC-silver(I) acetate compounds derived from 4,5-di-p-diisopropylphenyl- or 4,5-di-p-chlorophenyl-1H-imidazole
Streciwilk, Wojciech,Cassidy, Jennifer,Hackenberg, Frauke,Müller-Bunz, Helge,Paradisi, Francesca,Tacke, Matthias
, p. 88 - 99 (2014)
4,5-Di(p-isopropylphenyl)-1H-imidazole (2a) and 4,5-di(p-chlorophenyl)-1H- imidazole (2b) were prepared from the appropriately substituted benzoin precursors and then reacted with five p-substituted benzyl halide derivatives through N-dibenzylation to the
Benzoin Radicals as Reducing Agent for Synthesizing Ultrathin Copper Nanowires
Cui, Fan,Dou, Letian,Yang, Qin,Yu, Yi,Niu, Zhiqiang,Sun, Yuchun,Liu, Hao,Dehestani, Ahmad,Schierle-Arndt, Kerstin,Yang, Peidong
, p. 3027 - 3032 (2017)
In this work, we report a new, general synthetic approach that uses heat driven benzoin radicals to grow ultrathin copper nanowires with tunable diameters. This is the first time carbon organic radicals have been used as a reducing agent in metal nanowire synthesis. In-situ temperature dependent electron paramagnetic resonance (EPR) spectroscopic studies show that the active reducing agent is the free radicals produced by benzoins under elevated temperature. Furthermore, the reducing power of benzoin can be readily tuned by symmetrically decorating functional groups on the two benzene rings. When the aromatic rings are modified with electron donating (withdrawing) groups, the reducing power is promoted (suppressed). The controllable reactivity gives the carbon organic radical great potential as a versatile reducing agent that can be generalized in other metallic nanowire syntheses.
Synthesis of thiazolium salts and their screening for catalytic activity
Lee, Seul Ki,Kim, Do Joong,Park, Jin Kyoon
, p. 1311 - 1315 (2015)
A facile synthetic method to prepare thiazolium-based ionic liquids in high yield was developed. The direct alkylation of thiazole was performed using a trialkyl orthoester as both the alkyl donor and the solvent. The synthesized thiazolium salts were sub
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.).
N-PEGylated Thiazolium Salt: A Green and Reusable Homogenous Organocatalyst for the Synthesis of Benzoins and Acyloins
Haghighi, Ali Javaheri,Mokhtari, Javad,Karimian, Khashayar
, p. 1646 - 1652 (2020/10/19)
N-PEGylated-thiazolium salt is used as efficient catalyst for the benzoin condensation. The catalyst was synthesized by reaction of activated polyethylene glycol 10,000 (PEG-10000) with 4-methyl-5-thiazoleethanol (sulfurol). Reaction mixture undergoes temperature-assisted phase transition and catalyst separated by simple filtration. After reaction course, catalyst can be recycled and reused without any apparent loss of activity which makes this process cost effective and hence ecofriendly. Synthesized benzoins and acyloins by this method have been characterized on the basis of melting point and 1H-NMR spectral studies. Graphic Abstract: [Figure not available: see fulltext.]
Development of Imidazoline-2-one Derivatives as Potential Antifungal and Anthelminthic Agents: in silico and in vitro Evaluation
Chilamakuru, Naresh Babu,Mallela, Vijaya Jyothi,Peraman, Ramalingam,Shaik, Shakir Basha,Simham, Venu,Singirisetty, Triveni
, p. 423 - 433 (2021/11/24)
Based on appropriate values of synthetic accessibility concerning from ADMET properties and docking scores by docking against proteins 3OZU and 1OJ0, a series of 4,5-diphenyl-1H-imidazol-2-ones (I1?15) were synthesized. The key intermediate, 2-hydroxy-1,2-disubstitutedethanones (E1?15) were prepared by benzoin condensation using 2:1 ratio of aromatic aldehydes and thiamine in the presence of alkali. Further, these cyclized ethanones (E1?15) were treated with urea to yield 4,5-diphenyl-1H-imidazol-2-one derivatives (I1?15) and were characterized by IR,1H NMR, Mass spectra, and CHNO analysis. The synthesized compounds were screened for their anthelmintic potential on Pheretima Posthuma along with standard albendazole, and antifungal activity (minimum inhibitory concentration method) on Candida albicans and Aspergillus niger along with standard miconazole. The results revealed that among all the tested compounds I3, I4, and I7 show considerable synthetic accessibility, docking scores, anthelminthic, and antifungal activity.
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
N-Heterocyclic Carbene Acyl Anion Organocatalysis by Ball-Milling
Nicholson, William I.,Seastram, Alex C.,Iqbal, Saqib A.,Reed-Berendt, Benjamin G.,Morrill, Louis C.,Browne, Duncan L.
, p. 131 - 135 (2019/12/11)
The ability to conduct N-heterocyclic carbene-catalysed acyl anion chemistry under ball-milling conditions is reported for the first time. This process has been exemplified through applications to intermolecular-benzoin, intramolecular-benzoin, intermolecular-Stetter and intramolecular-Stetter reactions including asymmetric examples and demonstrates that this mode of mechanistically complex organocatalytic reaction can operate under solvent-minimised conditions.
1-butyl-3-methylimidazolium bromide as a solvent and precatalyst for stetter reaction
Phungpis, Baramee,Hahnvajanawong, Viwat
, p. 2028 - 2032 (2020/09/02)
Stetter reaction between aromatic aldehydes and acrylonitrile/ethyl acrylate performing in [Bmim]Br in the presence of NaOH is described. N-Heterocyclic carbene (NHC) generates in situ is shown to be an efficient catalyst. Benzoin condensation also occured as side reaction.
The Direct Conversion of α-Hydroxyketones to Alkynes
Ghiringhelli, Francesca,Nattmann, Lukas,Bognar, Sabine,Van Gemmeren, Manuel
, p. 983 - 993 (2019/01/24)
Alkynes are highly important functional groups in organic chemistry, both as part of target structures and as versatile synthetic intermediates. In this study, a protocol for the direct conversion of α-hydroxyketones to alkynes is reported. In combination with the variety of synthetic methods that generate the required starting materials by forming the central C-C bond, it enables a highly versatile fragment coupling approach toward alkynes. A broad scope for this novel transformation is shown alongside mechanistic insights. Furthermore, the utility of our protocol is demonstrated through its application in concert with varied α-hydroxyketone syntheses, giving access to a broad spectrum of alkynes.
