635-90-5Relevant academic research and scientific papers
Synthesis of pyrrole by 1,5,3,7-diazadiphosphocine-1,5-dicarboxylic acid as acid catalyst
Lee,Lee,Jung,Hahn
, p. 2257 - 2259 (2015)
As a part of research program related to the synthetic study of pharmacologically interesting compounds and good chelating agent for transition metal ion, we here report the synthesis of an unusual medium-sized ring heterocyclic ligand with mixed carboxylic-amino-phosphonic donating group. We have synthesized 3,7-dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphosphocine-1,5-diacetic acid (1a), 2-[5-(1,2-dicarboxyethyl-3,7-dihydroxy-3,7-dioxo-3[1,5,3,7]diazadiphosphocan-1-yl)-succinic acid (1b) and 3,7-dihydroxy-3,7-diox-operhydro-1,3,5,7-diazadiphosphocine-1,5-di-(2-glutaric acid) (1c). In order to analyze reactivity of synthesized dicarboxylic acids 1a-c as acid catalysts, we tried reactions of pyrrole formation according to acid variation. We know that the catalytic ability of synthesized dicarboxylic acids (1a-c) are very good at pyrrole formation reaction.
Synthesis and characterization of nano-cellulose immobilized phenanthroline-copper (I) complex as a recyclable and efficient catalyst for preparation of diaryl ethers, N-aryl amides and N-aryl heterocycles
Aghili, Nora,Hosseinzadeh, Rahman,Mavvaji, Mohammad
, (2022/01/03)
Functionalized nanocellulose was prepared and employed for immobilization of phenanthroline-copper(I) complex to afford cellulose nanofibril grafted heterogeneous copper catalyst [CNF-phen-Cu(I)]. This nanocatalyst was well characterized using FT-IR, NMR, XRD, CHNS, AAS, TGA, EDX and SEM. The activities of the synthesized catalyst were examined in the synthesis of diaryl ethers via C-O cross-coupling of phenols and aryl iodides, as well as, the preparation of N-aryl amides and N-aryl heterocycles through C-N cross-coupling of amides and N-H heterocycle compounds with aryl halides. In this trend, various substrates containing electron-donating and electron-withdrawing groups were exploited to evaluate the generality of this catalytic protocol. Accordingly, the catalyst demonstrated remarkable catalytic efficiency for both C-N and C-O cross-coupling reactions, thereby resulting in good to excellent yields of the desired products. Furthermore, the recoverability experiments of the catalyst showed that it can be readily retrieved by simple filtration and successfully reused several times with negligible loss of its catalytic activity.
L-Proline N-oxide dihydrazides as an efficient ligand for cross-coupling reactions of aryl iodides and bromides with amines and phenols
Ding, Zhiqiang,Nie, Nan,Chen, Tian,Meng, Lingxin,Wang, Gongshu,Chen, Zhangpei,Hu, Jianshe
supporting information, (2020/12/21)
A novel catalytic system based on L-proline N-oxide/CuI was developed and applied to the cross-coupling reactions of various N- and O- nucleophilic reagents with aryl iodides and bromides. This strategy featured in the employment of an-proline derived dihydrazides N-oxide compound as the superior supporting ligand. By using this protocol, a variety of products, including N-arylimidazoles, N-arylpyrazoles, N-arylpyrroles, N-arylamines, and aryl ethers, were synthesized with up to 99% yield.
Functionalization of superparamagnetic Fe3O4@SiO2 nanoparticles with a Cu(II) binuclear Schiff base complex as an efficient and reusable nanomagnetic catalyst for N-arylation of α-amino acids and nitrogen-containing heterocycles with aryl halides
Sardarian,Kazemnejadi,Esmaeilpour
, (2020/10/20)
Fe3O4@SiO2 nanoparticles was functionalized with a binuclear Schiff base Cu(II)-complex (Fe3O4@SiO2/Schiff base-Cu(II) NPs) and used as an effective magnetic hetereogeneous nanocatalyst for the N-arylation of α-amino acids and nitrogen-containig heterocycles. The catalyst, Fe3O4@SiO2/Schiff base-Cu(II) NPs, was characterized by Fourier transform infrared (FTIR) and ultraviolet-visible (UV-vis) analyses step by step. Size, morphology, and size distribution of the nanocatalyst were studied by transmission electron microscopy (TEM), scanning electron microscopy (SEM), and dynamic light scatterings (DLS) analyses, respectively. The structure of Fe3O4 nanoparticles was checked by X-ray diffraction (XRD) technique. Furthermore, the magnetic properties of the nanocatalyst were investigated by vibrating sample magnetometer (VSM) analysis. Loading content as well as leaching amounts of copper supported by the catalyst was measured by inductive coupled plasma (ICP) analysis. Also, thermal studies of the nanocatalyst was studied by thermal gravimetric analysis (TGA) instrument. X-ray photoelectron spectroscopy (XPS) analysis of the catalyst revealed that the copper sites are in +2 oxidation state. The Fe3O4@SiO2/Schiff base-Cu(II) complex was found to be an effective catalyst for C–N cross-coupling reactions, which high to excellent yields were achieved for α-amino acids as well as N-hetereocyclic compounds. Easy recoverability of the catalyst by an external magnet, reusability up to eight runs without significant loss of activity, and its well stability during the reaction are among the other highlights of this catalyst.
Copper nanoparticle anchored biguanidine-modified Zr-UiO-66 MOFs: a competent heterogeneous and reusable nanocatalyst in Buchwald-Hartwig and Ullmann type coupling reactions
Veisi, Hojat,Neyestani, Narges,Pirhayati, Mozhgan,Ahany Kamangar, Sheida,Lotfi, Shahram,Tamoradi, Taiebeh,Karmakar, Bikash
, p. 22278 - 22286 (2021/07/02)
We have designed a functionalized metal-organic framework (MOF) of UiO topology as a support, with an extremely high surface area, adjustable pore sizes and stable crystalline coordination polymeric structure and implanted copper (Cu) nanoparticles thereon. The core three dimensional Zr-derived MOF (UiO-66-NH2) was modified with a biguanidine moiety following a covalent post-functionalization approach. The morphological and physicochemical features of the material were determined using analytical methods such as FT-IR, SEM, TEM, EDX, atomic mapping, XRD and ICP-OES. The SEM and XRD results justified the unaffected morphology of Zr-MOF after structural modifications. The as-synthesized UiO-66-biguanidine/Cu nanocomposite was catalytically explored in the aryl and heteroaryl Buchwald-Hartwig C-N and Ullmann type C-O cross coupling reactions with excellent yields. A library of biaryl amine and biaryl ethers was synthesized over the catalyst under mild and green conditions. Furthermore, the catalyst was isolated by centrifugation and recycled 11 times with no significant copper leaching or change in its activity.
BENZOXAZOLE DERIVATIVES AND FLUORESCENT MATERIAL COMPRISING THE SAME
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Paragraph 0182-0186, (2021/07/13)
A benzoxazole derivative represented by Structural Formula 1 is provided. Thus, the present invention is not limited thereto. A fluorescent material is provided to remarkably improve fluorescence yield, to have excellent dyeing property and dispersibility, to minimize environmental pollution and to improve economic feasibility. Structural 1.
A solvent-free manganese(II) -catalyzed Clauson-Kaas protocol for the synthesis of N-aryl pyrroles under microwave irradiation
Anilkumar, Gopinathan,Meera, Gopinadh,Rohit, Kizhakkekuttu Radhakrishnan
supporting information, (2021/10/12)
The first manganese-catalyzed modified Clauson-Kaas reaction for N-substituted pyrrole synthesis using 2,5-dimethoxytetrahydrofuran with variously substituted aromatic amines has been developed (up to 89% yield). This interesting neat strategy is free from additives including co-catalysts, ligands, and acids. Relatively low cost, environmentally benign, and handy Mn(NO3)2·4H2O is employed as the catalyst under microwave conditions with a very short reaction time (20?min). The above qualities attest to the green nature of this reaction.
Amidosulfonic acid supported on graphitic carbon nitride: novel and straightforward catalyst for Paal–Knorr pyrrole reaction under mild conditions
Azhdari, Asieh,Azizi, Najmedin,Sanaeishoar, Haleh,Tahanpesar, Elham
, p. 625 - 634 (2021/05/12)
A novel heterogeneous acidic catalyst was prepared by in situ immobilization of amidosulfonic acid (NH2SO3H) on graphitic carbon nitride (g-C3N4) under hydrothermal conditions. The textural morphology of NH2SO3H/g-C3N4 nanocomposite was characterized via powder X-ray diffraction, FT-IR, TGA, EDX, and scanning electron microscopy. The spatial arrangement of the amidosulfonic acid on the surface of g-C3N4 leads to the construction of a unique solid acid structure, resulting in a substantial enhancement of catalytic activity toward a high efficient preparation of pyrroles by Paal–Knorr reaction. The reactions undergo completion readily with good to excellent yields, with simple purification in an environmentally friendly manner. The NH2SO3H/g-C3N4 nanocomposite can be readily recycled, and no noteworthy reduction in the catalytic activity detected after four runs. Graphic abstract: [Figure not available: see fulltext.]
Utilization of caffeine carbon supported cobalt catalyst in the tandem synthesis of pyrroles from nitroarenes and alkenyl diols
Balasubramaniam, Bhuvaneshwari,Dhara, Partha,Gupta, Raju K.,Kundu, Sabuj,Panja, Dibyajyoti,Sau, Anirban
, p. 244 - 254 (2021/09/07)
Employing bio-waste caffeine carbon-supported heterogeneous cobalt catalyst, synthesis of various substituted pyrrole derivatives is reported. In this methodology, pyrroles were synthesized through coupling between nitroarenes and alkenyl diols in a tandem manner. Among all the heterogeneous catalysts Co(OAc)2-CC-800 displayed the highest catalytic activity. Preparative scale synthesis of pyrroles and synthesis of anti-tubercular agent 5-(4-(1H-pyrrol-1-yl)phenyl)-1,3,4-oxadiazole-2-thiol revealed the practical applicability of this protocol. Several kinetic experiments and Hammett studies were conducted to understand the probable mechanism and electronic effects on this transformation.
Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation
K?nig, Burkhard,Wang, Hua,Wang, Shun
supporting information, p. 1653 - 1665 (2021/06/17)
Substantial effort is currently being devoted to obtaining photoredox catalysts with high redox power. Yet, it remains challenging to apply the currently established methods to the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive radical borylation reactions, thus expanding the available aryl radical precursor scope. Despite its high reducing power, the method has a broad substrate scope and good functional-group tolerance. Spectroscopic investigations and control experiments suggest the formation of a charge-transfer complex as the key step to activate the substrates.
