2272-45-9Relevant academic research and scientific papers
Highly Stereoselective Synthesis of Saccharin-Substituted β-Lactams via in Situ Generation of a Heterosubstituted Ketene and a Zwitterionic Intermediate as Potential Antibacterial Agents
Mortazavi, Zahra F. A.,Islami, Mohammad R.,Khaleghi, Moj
, p. 3034 - 3037 (2015)
Highly stereoselective synthesis of saccharin derivatives containing functionalized 2-azetidinone moiety was achieved starting from saccharin as an available precursor. The approach to these valuable heterocyclic scaffolds involves a formal [2π + 2π] cycloaddition between Schiff bases and the saccharinylketene as a novel ketene which was generated in situ and an electrocyclic reaction of a zwitterionic intermediate. The identification of the ketene was confirmed by reaction with the stable free radical TEMPO (TO?). Also, the antimicrobial activities of some new substituted saccharin against nine standard bacteria, four bacteria which were isolated from clinical samples and one yeast, were evaluated.
Development of a General Protocol to Prepare 2H-1,3-Benzoxazine Derivatives
Qi, Ji,Oliver, Steven F.,Xiao, Wensong,Song, Licheng,Brands, Karel M. J.
, p. 1547 - 1556 (2017)
A practical synthesis and detailed development process of 2H-1,3-benzoxazine derivatives catalyzed by aldimine and trifluoromethanesulfonic acid is described. A broad range of substrates with diverse steric and electronic properties were explored. Aliphatic/aromatic/heteroaromatic substrates all proceed well under conditions which have been optimized into a robust, scalable process.
Highly efficient and selective one-pot tandem imine synthesis via amine-alcohol cross-coupling reaction catalysed by chromium-based MIL-101 supported Au nanoparticles
Gülcan, Mehmet,Gumus, Ilkay,Karatas, Yasar,Ruzgar, Adem
, (2021)
One-pot tandem synthesis of imines from alcohols and amines is regarded as an effective, economic and green approach under mild conditions. In this work, Au nanoparticles (NPs) dispersed on MIL-101 (Au/MIL-101) were demonstrated as highly active and selective bifunctional heterogeneous catalyst for production of various imine derivatives with excellent yields, via amine-alcohol cross-coupling reaction at 343 K in an open flask under an Ar atmosphere. Various physicochemical techniques, including inductively coupled plasma optical emission spectroscopy (ICP-OES), powder X-ray diffraction (P-XRD), X-ray photoelectron spectroscopy (XPS) transmission electron microscopy (TEM) and N2 adsorption-desorption, were used to characterize of the Au/MIL-101 catalyst. The obtained bifunctional catalyst is highly active and selective towards one-pot imine formation and exhibited the highest TOF (30.15-51.47 h?1) among all the ever-reported MOF-supported Au catalysts. The reaction mechanism of the imine formation from alcohol and amine over Au/MIL-101 catalyst was proposed. Mechanism experiment results demonstrate that Au NPs highly effective in activating oxidation of benzyl alcohol to benzaldehyde while the Lewis acid sites on MIL-101 catalyzed the second condensation step without interfering with the oxidation step. As a result, the excellent catalytic performance of Au/MIL-101 can be ascribed to the synergistic effect between Au NPs with Lewis acid sites in MIL-101.
The recognition of a diarylimine as a metabonate produced during incubation of N-benzyl-4-chloroaniline with hepatic microsomal preparations
Low,Ulgen,Gorrod
, p. 585 - 590 (1994)
Evidence is presented for the formation of N-benzylidene-4-chloroaniline as a metabonate during the metabolism of N-benzyl-4-chloroaniline. Control studies suggest that the diarylimine is formed as a chemical artifact from the debenzylation products (benzaldehyde and 4-chloroaniline). This novel observation indicates a possible pathway to amide formation from N-benzylanilines via diarylimines as intermediates.
Copper(i)-catalysed intramolecular hydroarylation-redox cross-dehydrogenative coupling ofN-propargylanilines with phosphites
Li, Guangzhe,Yu, Guo,Wang, Chengdong,Morita, Taiki,Zhang, Xuhai,Nakamura, Hiroyuki
supporting information, p. 113 - 116 (2021/12/29)
Intramolecular hydroarylation-redox cross-dehydrogenative coupling ofN-propargylanilines with phosphite diesters proceeded in the presence of Cu(i)-catalysts (20 mol%) to selectively give 2-phosphono-1,2,3,4-tetrahydroquinolines in good yields with 100% atomic utilization. P-H and two C-H bonds are activated at once and these hydrogen atoms are trapped by a propargylic triple bond in the molecule.
Designed pincer ligand supported Co(ii)-based catalysts for dehydrogenative activation of alcohols: Studies onN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines
Singh, Anshu,Maji, Ankur,Joshi, Mayank,Choudhury, Angshuman R.,Ghosh, Kaushik
supporting information, p. 8567 - 8587 (2021/06/30)
Base-metal catalystsCo1,Co2andCo3were synthesized from designed pincer ligandsL1,L2andL3having NNN donor atoms respectively.Co1,Co2andCo3were characterized by IR, UV-Vis. and ESI-MS spectroscopic studies. Single crystal X-ray diffraction studies were investigated to authenticate the molecular structures ofCo1andCo3. CatalystsCo1,Co2andCo3were utilized to study the dehydrogenative activation of alcohols forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines. Under optimized reaction conditions, a broad range of substrates including alcohols, anilines and ketones were exploited. A series of control experiments forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines were examined to understand the reaction pathway. ESI-MS spectral studies were investigated to characterize cobalt-alkoxide and cobalt-hydride intermediates. Reduction of styrene by evolved hydrogen gas during the reaction was investigated to authenticate the dehydrogenative nature of the catalysts. Probable reaction pathways were proposed forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines on the basis of control experiments and detection of reaction intermediates.
Photocatalytic one-pot multidirectional N-alkylation over Pt/D-TiO2/Ti3C2: Ti3C2-based short-range directional charge transmission
Jiang, Heyan,Sheng, Meilin,Li, Yue,Kong, Shuzhen,Bian, Fengxia
, (2021/05/17)
Visible-light-induced one-pot, multistep, and chemoselectivity adjustable reactions highlight the economical, sustainable, and green process. Herein, we report Pt nanoparticles dispersed on S and N co-doped titanium dioxide/titanium carbide (MXene) (3%Pt/
Direct synthesis of imines from nitro compounds and biomass-derived carbonyl compounds over nitrogen-doped carbon material supported Ni nanoparticles
Li, Bo,Wang, Yanxin,Chi, Quan,Yuan, Ziliang,Liu, Bing,Zhang, Zehui
, p. 4464 - 4471 (2021/03/15)
The selective synthesis of imines from biomass-derived chemicals over heterogeneous non-noble metal catalysts is of great importance for organic transformation. Herein, non-noble heterogeneous nitrogen-doped carbon supported Ni catalysts (abbreviated as Ni/CN-MgO-T, whereTrepresents the pyrolysis temperature) have been facilely prepared from the simple pyrolysis of Ni precursors and biomass, and Ni/CN-MgO-600 with the smallest size of Ni nanoparticles demonstrated the highest catalytic activity. The reductive coupling of nitroarenes and carbonyl compounds could be performed under mild conditions (80 °C, and 10 bar H2), affording structurally-diverse imines with high to excellent yields (84.2-98.1%). Thanks to the mild reaction conditions, the developed method showed good tolerance to other functional groups such as nitriles, halogen and vinyl groups.
Highly chemoselective synthesis of imine over Co/Zn bimetallic MOFs derived Co3ZnC-ZnO embed in carbon nanosheet catalyst
Li, Guangming,Li, Jingfang,Li, Weizuo,Li, Xuewei,Mao, Guijie,She, Wei,Wang, Jing
, p. 17 - 26 (2021/07/28)
One-pot direct synthesis of imines via reductive amination of nitroarenes with aromatic aldehydes remains a great challenge due in part to its over-hydrogenation of imines to secondary amines. Herein, a novel Co3ZnC and ZnO supported on N-doped carbon nanosheet catalyst with the thickness of ca. 5.0 nm was fabricated through the direct pyrolysis of a Co/Zn bimetallic MOFs at 500 °C (named as Co3ZnC-ZnO/NC-500). Surprisingly, the developed Co3ZnC-ZnO/NC-500 catalyst delivers 99.9 % conversion of nitrobenzene and 98.5 % selectivity to N-benzylideneaniline in one-pot reductive amination of nitrobenzene with benzaldehyde. Various characterizations (including as SEM, XRD, TEM, AFM, XPS, Raman and N2 adsorption–desorption) have revealed that the generated small size of Co3ZnC alloy, abundant structural defects, larger specific surface area (105.5 m2·g?1) as well as more basic sites are responsible for the outstanding catalytic activity of Co3ZnC-ZnO/NC-500 catalyst for tandem reaction. Moreover, the Co3ZnC-ZnO/NC-500 catalyst exhibits high stability during the recycling experiments without the loss of its catalytic activity. Notably, the results of contrast experiments have demonstrated that the intentional introduction of ZnO in Co3ZnC-ZnO/NC-500 catalyst plays a key role in the selectivity to N-benzylideneaniline in the tandem reaction. This study provides a new guideline for designing tandem catalysts with high selectivity.
One-Pot Synthesis of Schiff Bases by Defect-Induced TiO2- x-Catalyzed Tandem Transformation from Alcohols and Nitro Compounds
Chen, Liyong,Fang, Qiang,Shen, Xiaoshuang,Tong, Jing,Wang, Jinfeng,Wang, Yao,Zhang, Hui
supporting information, p. 10715 - 10721 (2021/07/26)
Schiff bases that are generally formed from condensation reactions of aldehydes (or ketones) and amino groups could also be produced by a photodriven one-pot tandem reaction between alcohols and nitro compounds, in our case. Herein, TiO2-x porous cages derived from NH2-MIL-125 by a self-sacrificing template route are used to study the organic transformation and exhibit 100% conversion efficiency of nitrobenzene and 100% selectivity for Schiff bases in the system of benzyl alcohol (5 mL) and nitrobenzene (41 μL) upon light irradiation, but hydrogen by dehydrogenation of benzyl alcohol cannot be detected. Successful occurrence of the organic transformation is mainly attributed to Ti(III)-oxygen vacancy associates. Surface oxygen vacancy-related Ti(III) sites are responsible for binding with nitro groups, and low-coordinated Ti5c sites selectively adsorb hydroxyl groups of benzyl alcohol. The Ti(III) and oxygen vacancy associates capture photogenerated electrons for achievement of multielectron reduction of nitrobenzene and the subsequent Schiff base condensation reaction with the as-formed benzaldehyde.
