- Tris(3,5-dimethylpyrazole)copper(II) nitrate: As an oxidation catalyst
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Tris(3,5-dimethylpyrazole)copper(II) nitrate (A) is a catalyst for mild oxidation of various organic substrates. It acts as catalyst for conversion of benzylamine to benzaldehyde in the presence of hydrogen peroxide. Various benzylic alcohols are converted to corresponding aldehydes and acids by the catalytic amount of the complex (A) with hydrogen peroxide at room temperature. The complex also catalyses dimerisation of 2,6-dimethylphenol and thiophenol. The thermal decomposition of tris(3,5-dimethylpyrazole)copper(II) nitrate at 500°C gives CuO having the monoclinic crystal system. The cyclic voltammogram of the complex tris-(3,5-dimethylpyrazole)copper(II) nitrate shows a quasi-reversible redox cycle at -101 mV (E1/2) versus the Ag/AgCl electrode (+ve scan; scan speed 100 mV/s). The ΔE between anodic and cathodic peaks is 110 mV (ipa/ipc = 1.2).
- Sharma, Sagar,Barooah, Nilotpal,Baruah, Jubaraj B.
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- Selective Synthesis of 3-(α,α-Dibromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one as an Excellent Precursor for the Synthesis of 2-Substituted 4-(4-Hydroxy-6-methyl-2H-2-oxopyran-3-yl)thiazoles as Antimicrobial and Antifungal Agents
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A selective synthesis of 3-(α,α-dibromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one (3) has been achieved by bromination of DHA using CuBr2/CHCl3-EtOAc. The reaction of 3 with different thioureas/thiomides/thiosemicarbazide offers a convenient and efficient method for the syntheses of 2-substituted 4-(4-hydroxy-6-methyl-2H-2-oxopyran-3-yl)thiazoles. These thiazoles were evaluated for their antimicrobial and antifungal activity.
- Kapoor, Jitander K.,Prakash, Richa,Kumar, Ajay,Saini, Deepika,Arora, Loveena
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- Pyrazolylamidino ligands from coupling of acetonitrile and pyrazoles: A systematic study
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Mixed pyrazole-acetonitrile complexes, both neutral fac-[ReBr(CO)3(NCMe)(pzH)] (pzH = pzH, pyrazole; dmpzH, 3,5-dimethylpyrazole; or indzH, indazole) and cationic fac-[Re(CO)3(NCMe)(pzH)2]A (A = BF4, ClO4, or OTf), are described. Their role as the only starting products to obtain final pyrazolylamidino complexes fac-[ReBr(CO)3(NH=C(Me)pz-κ2N,N)] and fac-[Re(CO)3(pzH)(NH=C(Me)pz-κ2N,N)]A, respectively, is examined. Other products involved in the processes, such as fac-[ReBr(CO)3(pzH)2], fac-[Re(CO)3(NCMe)(NH=C(Me)pz-κ2N,N)]A, and fac-[Re(CO)3(pzH)2(OTf)] are also described. Warming CD3CN solutions of fac-[Re(CO)3(NCMe)(pzH)2]A at 40 °C gives cleanly the pyrazolylamidino complexes [Re(CO)3(pzH)(NH=C(Me)pz-κ2N,N)]A as the only products, pointing to an intramolecular process. This is confirmed by carrying out reactions in the presence of one equivalent of a pyrazole different from that coordinated, which affords complexes where the pyrazolylamidino ligand contains only the pyrazole previously coordinated. When the reactions lead to an equilibrium mixture of the final and starting products, the reverse reaction gives the same equilibrium mixture, which indicates that the coupling reaction of pyrazoles and nitriles to obtain pyrazolylamidino ligands is a reversible intramolecular process. A systematic study of the possible factors which may affect the reaction gives the following results: (a) the yields of the direct reactions are higher for lower temperatures; (b) the tendency of the pyrazoles to give pyrazolylamidino complexes follows the sequence indzH > pzH > dmpzH; and (c) the reaction rates do not depend on the nature of the anion even when a large excess is added. The presence of a small amount of aqueous solution of NaOH catalyzes the reaction. Thus, addition of 0.5-1% of NaOH (aq) to solutions of fac-[ReBr(CO)3(NCMe)(pzH)] (in CD3CN) or fac-[Re(CO)3(NCMe)(pzH)2]A (in CD3CN, CD3NO2 or (CD3)2CO) allowed the syntheses of the corresponding pyrazolylamidino complexes [ReBr(CO)3(NH=C(Me)pz-κ2N,N)] or [Re(CO)3(pzH)(NH=C(Me)pz-κ2N,N)]A with better yields, more rapidly, and in milder conditions.
- Gmez-Iglesias, Patricia,Arroyo, Marta,Bajo, Sonia,Strohmann, Carsten,Miguel, Daniel,Villafae, Fernando
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- Halocarbon Encapsulation via Halogen···?€ Interactions in a Bispyrazole-Based Cryptand
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A novel bispyrazole-based expanded cryptand was synthesized via Schiff base condensation reaction having an internal cavity of 160 ?3 with a hydrophobic nature. The cryptand features electron-rich multiple pyrazole rings for enhanced weak noncovalent interactions with the guest molecules. The host-guest capabilities of the cryptand were investigated for encapsulation of the most inactive halogen bond donor molecules (having small σ-hole size), namely, CH2Cl2, CHCl3, CCl4, C2HCl3, C2H4Cl2, and C2H4Br2. Analysis of crystal structures clearly revealed that halogen bonding (C-Cl/Br···π (pyrazole)) and hydrogen bonding (C-H···π(pyrazole)) interactions played a key role in stabilizing the halogenated guests inside the hydrophobic cavity of cryptand. At the same time, the cage is efficiently able to exclude hydrophilic solvent molecules, like, water and methanol, suggesting the hydrophobic nature of the cavity. Due to the comparably large σ-hole in C2H4Br2, it showed the strongest halogen bonding interaction with the host cryptand, while weakest interaction was found for the CH2Cl2 guest which has the smallest size σ-hole. Furthermore, the cryptand is able to adjust its central cavity according to the size of the guest. The biggest cavity size was found for the C2H4Br2 guest, while smallest size was found for the CH2Cl2 guest molecule. This study sheds more light on the interaction of halogenated solvents via halogen and hydrogen bonding, which is critical in understanding and controlling chemical reactions where solvent effects play an important role.
- Verma, Ashish,Tomar, Kapil,Bharadwaj, Parimal K.
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- Pd-Catalyzed Asymmetric Dearomatization of Indoles via Decarbonylative Heck-Type Reaction of Thioesters
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We report herein a palladium-catalyzed ligand-promoted asymmetric dearomatization of indoles via the decarbonylation of thioesters and the subsequent reductive Heck reaction. This protocol provides a facile and efficient way to construct an aza-quaternary stereocenter at the C2 position of indolines. A variety of functional groups and substitutions could be well tolerated, affording the substituted indolines with high enantioselectivities.
- Han, Ming-Liang,Huang, Wei,Liu, Yu-Wen,Liu, Min,Xu, Hui,Xiong, Hai,Dai, Hui-Xiong
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- Synthesis and Cyclizations of N-(Thieno[2,3-b]pyridin-3-yl)cyanoacetamides
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3-Aminothieno[2,3-b]pyridine-2-carboxylic acid esters readily reacted with 3,5-dimethyl-1-(cyanoacetyl)-1H-pyrazole to give previously unknown N-(thieno[2,3-b]pyridin-3-yl)cyanoacetamides. Reactions of the latter with 2-(arylmethylidene)malononitriles were nonselective, and mixtures of different heterocyclization products were generally formed. The cyclization of ethyl 4,6-dimethyl-3-[(cyanoacetyl)amino]thieno[2,3-b]-pyridine-2-carboxylate afforded 2,4-dihydroxy-7,9-dimethylthieno[2,3-b : 4,5-b′]dipyridine-3-carbonitrile whose tautomeric equilibrium was studied by DFT quantum chemical calculations. In silico analysis of biological activity of the synthesized compounds was performed.
- Chigorina,Bespalov,Dotsenko
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- Nickel (II) and cobalt (II) complexes with bidentate nitrogen-sulfur donor pyrazole derivative ligands: Syntheses, characterization, X-ray structure, electrochemical studies, and antibacterial activity
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The synthesis, characterization, antibacterial activity and cyclic voltammetry of bidentate N,S donor pyrazole derivative ligands abbreviated as Na(EtNCSPz) (1), Na(PhNCSPz) (2), Na(PhNCSPzme2) (3), Na(PhNCSPzme3) (4) and their metal complexes with Ni(II) and Co(II) metal ions are reported, where Pz = pyrazole, Pzme2 = 3,5-dimethylpyrazole and Pzme3 = 3,4,5-trimethylpyrazole. All of the synthesized ligands and complexes have been characterized by physicochemical and spectroscopic methods and the crystal structures of [Ni(EtNCSPz)2] (1a) and [Ni(PhNCSPzMe3)2] (4a) have been determined by X-ray diffraction analysis. The X-ray crystal structure of both the complexes describe a square planar coordination geometry. The electrochemical studies show that the synthesized complex is an electrochemically active species, furthermore, substitution electron donating groups on the ligands shift the reduction and oxidation potentials to negative values. Antibacterial activity results indicate these complexes possess high activity against gram-positive and gram-negative bacteria compare to the free ligands.
- Soltani, Behzad,Ghorbanpour, Monireh,Ziegler, Christopher J.,Ebadi-Nahari, Mostafa,Mohammad-Rezaei, Rahim
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- Predicting the catalytic activity of azolium-based halogen bond donors: an experimentally-verified theoretical study
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This report demonstrates the successful application of electrostatic surface potential distribution analysis for evaluating the relative catalytic activity of a series of azolium-based halogen bond donors. A strong correlation (R2> 0.97) was observed between the positive electrostatic potential of the σ-hole on the halogen atom and the Gibbs free energy of activation of the model reactions (i.e., halogen abstraction and carbonyl activation). The predictive ability of the applied approach was confirmed experimentally. It was also determined that the catalytic activity of azolium-based halogen bond donors was generally governed by the structure of the azolium cycle, whereas the substituents on the heterocycle had a limited impact on the activity. Ultimately, this study highlighted four of the most promising azolium halogen bond donors, which are expected to exhibit high catalytic activity.
- Bolotin, Dmitrii S.,Il'in, Mikhail V.,Novikov, Alexander S.,Suslonov, Vitalii V.,Sysoeva, Alexandra A.
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p. 7611 - 7620
(2021/09/22)
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- High Proton Conductivity of a Cadmium Metal-Organic Framework Constructed from Pyrazolecarboxylate and Its Hybrid Membrane
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A new type of metal-organic framework, [Cd2(pdc)(H2O)(DMA)2]n (pdc = 3,5-pyrazoledicarboxylic acid; DMA = dimethylamine), named Cd-MOF, was synthesized and characterized. There are regular rectangular pore channels containing a large number of dimethylamine cations in the crystal structure. AC impedance test results show the proton conductivity of Cd-MOF reaches 1.15 × 10-3 S cm-1 at 363 K and 98% RH. In order for its application in fuel cells, the Cd-MOF was introduced into a sulfonated polyphenylene oxide matrix to prepare a hybrid membrane, and the proton conductivity of the hybrid membrane has a high value of 2.64 × 10-1 S cm-1 at 343 K and 98% RH, which is higher than those of most MOF polymer hybrid membranes. The proton conductivity of the hybrid membrane of the SPPO polymer still maintains a certain degree of stability in a wide temperature range. To the best of our knowledge, it is the first proton exchange membrane that combines pyrazolecarboxylate cadmium MOFs and an SPPO polymer with high proton conductivity and good stability. This research may help to further develop the application of MOFs in the field of proton exchange membrane fuel cells.
- Wang, Feng-Dong,Su, Wen-Hui,Zhang, Chen-Xi,Wang, Qing-Lun
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supporting information
p. 16337 - 16345
(2021/11/01)
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- Pyrazole-Mediated C-H Functionalization of Arene and Heteroarenes for Aryl-(Hetero)aryl Cross-Coupling Reactions
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Herein we introduce a transition-metal-free protocol that involves a commercially available, inexpensive pyrazole molecule to conduct C-C cross-coupling reactions at room temperature via a radical pathway. Using this method, an aryldiazonium salt has been coupled to a wide range of arenes and heteroarenes including benzene, mesitylene, thiophene, furan, benzoxazole to result the corresponding biaryl products. The full reaction mechanism is elucidated along with the crystallographic probation of an active initiator species. A potassium-stabilized deprotonated pyrazole steers single-electron transfer to the substrate and behaves as an initiator for the reaction.
- Kundu, Abhishek,Dey, Dhananjay,Pal, Subhankar,Adhikari, Debashis
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p. 15665 - 15673
(2021/11/16)
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- Green, homogeneous oxidation of alcohols by dimeric copper(II) complexes
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Three pyrazole derivatives, 3,5-dimethyl-1H-pyrazole (DMPz) (I), 3-methyl-5-phenyl-1H-pyrazole (MPPz) (II), and 3,5-diphenyl-1H-pyrazole (DPPz) (III), were prepared via reacting semicarbazide hydrochloride with the acetylacetone, 1-phenylbutane-1,3-dione, and 1,3-diphenylpropane-1,3-dione, respectively. Complexes 1–3 were isolated by reacting CuCl2·2H2O with I–III, respectively, and characterized by CHNS elemental analyses, FT-IR, UV-Vis, 1H and 13C NMR, EPR spectra, and TGA/DTA. Molecular structures of the pyrazole derivatives I–III and copper(II) complexes 2 and 3 were studied through single-crystal XRD analysis to confirm their molecular structures. Overlapping of hyperfine splitting in the EPR spectra of the dimeric copper(II) complexes 1–3 indicates that both copper centers do not possess the same electronic environment in solution. The copper(II) complexes are dimeric in solid state as well as in solution and catalyze the oxidation of various primary and secondary alcohols selectively. Catalysts 1–3 show more than 92% product selectivity toward ketones during the oxidation of secondary alcohols. Surprisingly primary alcohols, which are relatively difficult to oxidize, produce carboxylic acid as a major product (48%–90% selectivity) irrespective of catalytic systems. The selectivity for carboxylic acid rises with decreasing the carbon chain length of the alcohols. An eco-friendly and affordable catalytic system for oxidation of alcohols is developed by the utilization of H2O2, a green oxidant, and water, a clean and greener solvent, which is a notable aspect of the study.
- Maurya, Abhishek,Haldar, Chanchal
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p. 885 - 904
(2020/12/18)
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- Preparation method of dinotefuran
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The invention provides a preparation method of dinotefuran, and belongs to the field of organic synthesis. The invention provides a preparation method of dinotefuran, which is characterized by comprising the following steps: step 1, adding a compound I, a compound II and a solvent into a reaction container, heating to 50 DEG C which is the reflux temperature of the solvent, reacting for 1-24 hours, then adding tetrahydrofuran-3-methylamine, and continuously reacting for 1-24 hours to obtain a reaction solution; and 2, cooling the reaction solution to 0-20 DEG C, standing, filtering, separating the solid and filtrate, and purifying the solid to obtain dinotefuran, wherein the structural formula of the compound I is shown in the specification, the structural formula of the compound II is shown in the specification, and R1 and R2 are independently selected from any one of H, C1-C5 alkyl and C1-C5 alkyl substituted by at least one halogen atom. According to the invention, a brand new dinotefuran synthesis route is developed, the synthesis route is greatly shortened, and the production efficiency is improved.
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Paragraph 0013; 0054-0062; 0069-0074
(2021/08/07)
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- Copper (II) complexes with novel Schiff-based ligands: synthesis, crystal structure, thermal (TGA–DSC/FT-IR), spectroscopic (FT-IR, UV-Vis) and theoretical studies
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This study aimed to synthesize two novel Schiff-base ligands through the condensation between N-(2-aminoethyl)pyrazoles and 2-hydroxy-1-naphthaldehyde, which are: NaphPz ((E)-1-(((2-(1H-pyrazol-1-yl)ethyl)imino)methyl)naphthalen-2-ol)) and NaphDPz ((E)-1-(((2-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl)imino)methyl)naphthalen-2-ol). These novel pyrazole-imines were synthesized, characterized and used as copper (II) ion complexing agents. Different synthetic routes have been adapted to obtain the [Cu(NaphPz)Cl], [Cu(NaphDPz)Cl] and [Cu(NaphPz)2] complexes in the solid state, the first two in the crystalline form and the latter as a powder. The minimum metal–ligand stoichiometry for the three complexes was defined by TGA–DSC thermoanalytical data and by single-crystal X-ray diffraction for the crystalline samples which belong to the P21/n space group. The products of the thermal decomposition of the material were also monitored by TGA–DSC/FT-IR in air and N2 atmospheres in order to suggest how thermal decomposition of the organic portion of the complex occurs. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations compared to experimental results (UV-Vis and FT-IR) show a high degree of correlation. From HOMO/LUMO orbitals, the main major charge distributions, responsible for the absorption bands of the complexes, were determined.
- Campos, Guilherme Fava,Martins, Gabriel Rodrigues,Moreira, Jeniffer Meyer,Schwalm, Cristiane Storck,Tirloni, Bárbara,de Campos Pinto, Leandro Moreira,de Carvalho, Cláudio Teodoro
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- Synthesis of 1,3,5-Trisubstituted Pyrazoles and Hydrazones Using Fe3O4?CeO2 Nanocomposite as an Efficient Heterogeneous Nanocatalyst
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Abstract: Pyrazoles and hydrazones, as two significant kinds of potentially bioactivecompounds, were produced with good to excellent yields by condensation ofβ-dicarbonyl compounds with hydrazines in aqueous media in the presence ofFe3O4?CeO2nanocomposite as an efficient heterogeneous nanocatalyst. The magneticnanocatalyst can readily be separated using an external magnet and reused atleast six times without significant loss in activity. The products werecharacterized by IR and 1H and13C NMR spectra.
- Hassani, H.,Jahani, Z.
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p. 485 - 490
(2020/04/27)
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- Synthesis of quinoxaline, benzimidazole and pyrazole derivatives under the catalytic influence?of biosurfactant-stabilized iron nanoparticles in water
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Abstract: We have reported the synthesis, characterization, and catalytic applications of amorphous iron nanoparticles (FeNPs) using aqueous leaves extract of renewable natural resource Boswellia serrata plant. Synthesized FeNPs were stabilized in situ by the addition of aqueous pod extracts of Acacia concinna as a biosurfactant (pH 3.11). The structural investigation of biosynthesized nanoparticles was performed using UV–visible spectroscopy, X-ray diffraction analysis, selected area electron diffraction, energy-dispersive X-ray spectroscopy, scanning electron microscopy, transmission electron microscopy, X-ray photoelectron spectroscopy, thermogravimetric analysis, and BET analysis. The FeNPs were amorphous in nature with average particle size ~ 19?nm and successfully employed as heterogeneous catalyst for the synthesis of quinoxaline, benzimidazole, and pyrazole derivatives in aqueous medium at ambient conditions. The FeNPs could be recycled up to five times with modest change in the catalytic activity. Graphic abstract: [Figure not available: see fulltext.].
- Arde, Satyanarayan M.,Patil, Audumbar D.,Mane, Ananda H.,Salokhe, Prabha R.,Salunkhe, Rajashri S.
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p. 5069 - 5086
(2020/09/02)
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- Novel one-dimensional polymeric Cu(II) complexes via Cu(II)-assisted hydrolysis of the 2,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)-6-methoxy-1,3,5-triazine pincer ligand: Synthesis, structure, and antimicrobial activities
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Two unexpected one-dimensional coordination polymers, [Cu(PT)(H2O)Cl]n 1 and [Cu2(BPT)(ClO4)3(H2O)4]n·2nH2O 2, of symmetrical triazine-based ligands were sy
- Soliman, Saied M.,El-Faham, Ayman,El Silk, Sobhy E.
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- Reductive dehalogenation and dehalogenative sulfonation of phenols and heteroaromatics with sodium sulfite in an aqueous medium
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Prototropic tautomerism was used as a tool for the reductive dehalogenation of (hetero)aryl bromides and iodides, or dehalogenative sulfonation of (hetero)aryl chlorides and fluorides, using sodium sulfite as the sole reagent in an aqueous medium. This protocol does not require a metal or phase transfer catalyst and avoids using organic solvent as the reaction medium. This method is especially suitable for substrates that readily tautomerize (such as 2-or 4-halogenated aminophenols and 4-halogenated resorcinols), for which dehalogenation or sulfonation proceeds under mild reaction conditions (≤60 °C). As sodium sulfite is an inexpensive, safe, and environmentally less hazardous reagent, this method has at least three potential applications: (i) in the deprotection of halogens as protecting groups, using sodium sulfite as a reducing agent; (ii) in the sulfonation of aromatic halides under mild reaction conditions avoiding hazardous and corrosive reagents/solvents; and (iii) in the transformation of toxic halogenated aromatics into less harmful compounds.
- Tomanová, Monika,Jedinák, Luká?,Canka?, Petr
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supporting information
p. 2621 - 2628
(2019/06/03)
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- Cu1.5PMo12O40-catalyzed condensation cyclization for the synthesis of substituted pyrazoles
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A convenient and direct approach has been developed for the preparation of pyrazole derivatives by the condensation cyclization of hydrazines/hydrazide and 1,3-diketones in the presence of Cu1.5PMo12O40 (0.33?mol%) under mild conditions (r.t.-60?°C, 10–30?min). Notably, the reaction was found to be scalable as 99% yield was obtained when the reaction was performed at a 5-mmol scale. This solvent-free and halogen-free catalytic system represents an effective economic and environmentally friendly method for the construction of pyrazoles.
- Yang, Guo-Ping,He, Xing,Yu, Bing,Hu, Chang-Wen
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- Biomimetic Cleavage of Aryl–Nitrogen Bonds in N-Arylazoles Catalyzed by Metalloporphyrins
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The cleavage of C–N single bonds of N-containing compounds provides either an excellent nitrogen source or an excellent carbon source. In this study, an efficient metalloporphyrins/H2O2 cleavage of C–N bonds of arylpyrazoles was investigated. The effects of different factors, including different catalysts, catalyst dosages, H2O2 dosages, reaction temperature and reaction time were studied. The experimental results showed that the optimal catalyst was FeTPPCl, and the yield of pyrazole derivatives could reach up to 12.3%, which was fourfold higher than hemin catalyzed reaction and closed to ceric ammonium nitrate catalyzed reaction, respectively. Compared with transition-metal-catalyzed and strong-oxidization cleavage of C–N bonds, this protocol is characterized by environmentally-friendly, stable, mild reaction conditions and simplified operation procedures. Graphical Abstract: [Figure not available: see fulltext.].
- Yu, Zongjiang,Zhai, Guoqing,Xian, Mo,Lu, Ming,Wang, Pengcheng,Jiang, Tao,Xu, Chao,Sun, Weizhi
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p. 2636 - 2642
(2018/06/20)
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- Method for breaking C-N bond through biomimetic catalysis in aryl nitrogen-containing compound
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The invention discloses a method for breaking a C-N bond through biomimetic catalysis in an aryl nitrogen-containing compound. A reaction system for breaking the C-N bond in the aryl nitrogen-containing compound through metalloporphyrin mimic enzyme biomimetic catalysis is used, and the preparation of the catalyst and the optimization of the reaction system are involved. Iron porphyrin, manganeseporphyrin and cobalt porphyrin are adopted as mimetic enzymes and H2O2 is used as an oxidant to respectively break the C-N bonds of arylpyrazole derivatives with different structures through catalyst,the yield of a nitrogen heterocyclic product can reach 15.2% to the largest content, and the yield is 4 times of that of bio-enzyme catalysis, and is close to the yield (20%) of cerium ammonium nitrate oxidation. The method has the advantages of simplicity, mildness, economy, and greenness compared with conventional oxidants or transition metal catalyst systems.
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Paragraph 0023; 0024; 0030; 0032; 0034; 0036; 0038; 0040
(2018/09/21)
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- Discovery of DS79182026: A potent orally active hepcidin production inhibitor
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Hepcidin has emerged as the central regulatory molecule of systemic iron homeostasis. Inhibition of hepcidin could be a strategy favorable to treating anemia of chronic disease (ACD). We report herein the synthesis and structure-activity relationships (SARs) of a series of benzisoxazole compounds as orally active hepcidin production inhibitors. The optimization study of multi kinase inhibitor 1 led to a potent and bioavailable hepcidin production inhibitor 38 (DS79182026), which showed serum hepcidin lowering effects in a mouse IL-6 induced acute inflammatory model.
- Fukuda, Takeshi,Goto, Riki,Kiho, Toshihiro,Ueda, Kenjiro,Muramatsu, Sumie,Hashimoto, Masami,Aki, Anri,Watanabe, Kengo,Tanaka, Naoki
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p. 3716 - 3722
(2017/07/27)
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- A two-valence sulfonyl isoxazole derivatives and use thereof
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The invention discloses a bi-titer sulfonyl isoxazole derivative in the technical field of organic compound weedicides, and application thereof. The bi-titer sulfonyl isoxazole derivative has a molecular structural formula shown as a general formula I. The invention further discloses a preparation method of the bi-titer sulfonyl isoxazole derivative. The bi-titer sulfonyl isoxazole derivative has very high activity of inhibiting weed growth and killing and removing weeds, and can be used in agricultural production, and is classified as a novel active component for weedicides.
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Paragraph 0010; 0018; 0025-0026
(2017/10/07)
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- Chiral Cadmium(II) Metal-Organic Framework from an Achiral Ligand by Spontaneous Resolution: An Efficient Heterogeneous Catalyst for the Strecker Reaction of Ketones
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A thermally stable cadmium-based chiral metal-organic framework (MOF), {[Cd2(L)(H2O)(DMF)]·3DMF·2H2O}n (1; DMF = N,N-dimethylformamide), has been synthesized from an achiral ligand by spontaneous resolution. The MOF features 1D open channels with a large density of active metal sites and has a 3,6-c binodal net with a rare sit 3,6-conn topology. The metal-bound water and DMF solvents could be easily removed along with the guest molecules in the lattice upon activation to afford the desolvated framework 1′. It exhibits microporous nature, as confirmed by the gas-sorption measurements with carbon dioxide uptake of 43.2 cm3 g-1 at 273 K. The open metal sites in the framework make it an outstanding heterogeneous catalyst in the Strecker reaction for the synthesis of α-aminonitriles in a solvent-free state at room temperature with excellent conversion yields.
- Verma, Ashish,Tomar, Kapil,Bharadwaj, Parimal K.
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supporting information
p. 13629 - 13633
(2017/11/24)
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- Synthesis and characterization of some symmetrical substituted 1-(2-chloroethyl)pyrazole-based chalcogenides
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The present paper describes the synthesis of some symmetrical substituted 1-(2-chloroethyl) pyrazole-based dichalcogenides and monochalcogenides by reacting different 3,4,5-trisubstituted 1-(2-chloroethyl) pyrazole derivatives with in situ prepared Na2E2 (E = S, Se, Te) and sodium hydrogen selenide, respectively. All compounds were fully characterized by different spectroscopic techniques, namely, IR, 1H, 13C, 77Se nuclear magnetic resonance, and mass spectrometry. X-ray crystal structure determination of 1,2-bis(2-(4-bromo-3,5-dimethyl-1H-pyrazol-1-yl)ethyl)diselane (10b) reveals intermolecular Se·N·H interactions between two molecules.
- Pundir,Mehta,Mobin,Bhasin
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- Versatile Tri(pyrazolyl)phosphanes as Phosphorus Precursors for the Synthesis of Highly Emitting InP/ZnS Quantum Dots
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Tri(pyrazolyl)phosphanes (5R1,R2) are utilized as an alternative, cheap and low-toxic phosphorus source for the convenient synthesis of InP/ZnS quantum dots (QDs). From these precursors, remarkably long-term stable stock solutions (>6 months) of P(OLA)3 (OLAH=oleylamine) are generated from which the respective pyrazoles are conveniently recovered. P(OLA)3 acts simultaneously as phosphorus source and reducing agent in the synthesis of highly emitting InP/ZnS core/shell QDs. These QDs are characterized by a spectral range between 530–620 nm and photoluminescence quantum yields (PL QYs) between 51–62 %. A proof-of-concept white light-emitting diode (LED) applying the InP/ZnS QDs as a color-conversion layer was built to demonstrate their applicability and processibility.
- Panzer, René,Guhrenz, Chris,Haubold, Danny,Hübner, René,Gaponik, Nikolai,Eychmüller, Alexander,Weigand, Jan J.
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supporting information
p. 14737 - 14742
(2017/10/23)
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- Application of Fe3O4@SiO2@sulfamic acid magnetic nanoparticles as recyclable heterogeneous catalyst for the synthesis of imine and pyrazole derivatives in aqueous medium
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Sulfamic acid supported on Fe3O4@SiO2 superpara magnetic nanoparticles was successfully applied as a recyclable solid acid catalyst with a large density of sulfamic acid groups for the synthesis of pyrazole derivatives, an important class of potentially bioactive compounds. The products are obtained in high yield from the one-pot reaction procedure involving dicarbonyl compounds and hydrazines/hydrazides. This new method totally avoids the use of toxic or expensive solvents and organic acids in this reaction.
- Zakerinasab,Nasseri,Hassani,Samieadel
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p. 3169 - 3181
(2016/04/05)
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- Synthesis, crystal structure and photophysical study of luminescent three-coordinate cuprous bromide complexes based on pyrazole derivatives
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The 1: 2 M-ratio reaction between cuprous bromide and pyrazole derivatives in toluene results in mononuclear Cu(I) complexes [CuBr(pyrazole)2]. The complexes have been characterized by 1H NMR spectroscopy and elemental analysis. The molecular structure, established by single-crystal X-ray diffraction, features a trigonal planar geometry around copper, with monodentate pyrazole derivatives. All the Cu(I) complexes are luminescent in the solid state at ambient temperature. Intense blue or blue-green emission in the solid state is observed for these complexes, with the maxima ranging from 431 to 493 nm. The observed photoluminescence could be ascribed to the metal-to-ligand charge-transfer excited states, probably mixed with some halide-to-ligand character. The microsecond lifetime scale of the complexes implies that these transitions arise from the triplet excited states.
- Wu, Fengshou,Tong, Hongbo,Wang, Kai,Zhang, Xiulan,Zhang, Jie,Wong, Wai-Kwok,Zhu, Xunjin
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p. 926 - 933
(2016/04/08)
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- Action of Some Nitrogen and Carbon Nucleophils on 4-Arylidene-1,3-oxazolones
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(Chemical Equation Presented) 1,3-Oxazolones 1 and 2 were reacted with hydrazine hydrate to afford the corresponding hydrazides 3 and 4. Treatment of the hydrazides withacetylacetone, acetonylacetone, ethyl acetoacetate and diethyl malonateyielded different heterocycles. However, oxazolones 1 and 2 reacted with methyl p-aminobenzoate to afford the imidazolones 5a,b which were converted into the hydrazide 3a or the triazinone derivative 6 upon treating with hydrazine hydrate. The structures of the newly synthesized compounds were established using IR, 1H-NMR, EIMS, and elemental analyses.
- Youssef, Ahmed S. A.,Kandeel, Kamal A.,Abou-Elmagd, Wael S. I.,Haneen, David S. A.
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p. 175 - 182
(2015/03/04)
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- PRODUCING METHOD OF NITROGEN-CONTAINING ORGANIC COMPOUND
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A hydrazine-carbon dioxide-binding compound or hydrazine derivatives 2 carbonyl group react with a compound having one or more nitrogen-containing organic for preparing the compounds of relates to method.
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Paragraph 0216; 0236-0238
(2016/12/01)
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- An efficient practical chemo-enzymatic protocol for the synthesis of pyrazoles in aqueous medium at ambient temperature
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An expeditious oxidative cyclocondensation reaction of hydrazines/hydrazides with 1,3-dicarbonyl compound was efficiently developed in aqueous medium using Saccharomyces cerevisae (baker's yeast) as a whole cell biocatalyst at room temperature. The method has been assigned using green chemistry measures and found to give a range of N-substituted pyrazoles with moderate to excellent yields (70-92%). The reaction progress was monitored by gas chromatography.
- Mane, Ananda,Salokhe, Prabha,More, Pallavi,Salunkhe, Rajashri
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- A modified and practical synthetic route to indazoles and pyrazoles using tungstate sulfuric acid
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Tungstate sulfuric acid-catalyzed Knorr reaction have been used as a simple, rapid, atom economic and green method for the synthesis of indazole and pyrazole derivatives based on the condensation of hydrazine derivatives and ss-dicarbonyl compounds under solvent-free conditions. It was found that the catalyst could be recovered and reused without significant loss of its activity. The use of this method provides a novel and improved modification of Knorr synthesis in terms of clean reaction profile, use of a safe catalyst and solvent-free conditions. A green method for the synthesis of indazole and pyrazole derivatives from the condensation of hydrazine derivatives with dicarbonyl compounds has been described. Tungstate sulfuric acid (TSA) catalyzed efficiently the reactions to give good yields.
- Rahmatzadeh, S. Setareh,Karami, Bahador,Khodabakhshi, Saeed
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- Tandem copper (Cu) catalysed N-arylation-vinylogous nitroaldol condensation of 3,5-disubstituted 4-nitropyrazoles
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A tandem process involving copper catalysed N-arylation and vinylogous nitroaldol condensation is described. The reaction of 3,5-dialkyl substituted 4-nitropyrazoles and ortho-halo substituted (hetero)aryl aldehydes or ketones furnished 3-nitropyrazolo[1,5-a]quinoline and heteroaryl-fused 3-nitropyrazolo[1,5-a]pyridine derivatives in moderate to high yields.
- Obulesu, Owk,Nanubolu, Jagadeesh Babu,Suresh, Surisetti
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supporting information
p. 8232 - 8240
(2015/08/03)
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- Cellulose sulfuric acid as a bio-supported and efficient solid acid catalyst for synthesis of pyrazoles in aqueous medium
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A convenient and practical method was described for the regioselective synthesis of pyrazoles from hydrazines/hydrazides and 1,3-dicarbonyl compounds via the Knorr synthesis in water with cellulose sulfuric acid (CSA) as a biopolymer-based solid acid catalyst. Various hydrazines and hydrazides were reacted with 1,3 diketones and the desired pyrazoles were obtained in high yields. The reaction of less reactive hydrazines with 1,3-dicarbonyl compounds stopped at the corresponding hydrazone derivatives. Hydrazides were employed with β-ketoester, and imine adducts were the only isolated product. Simple isolation of products, mild reaction conditions, reusability of solid acid catalysts and short reaction times are advantages of this green procedure. This journal is
- Nasseri, Mohammad Ali,Salimi, Mehri,Esmaeili, Abbas Ali
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p. 61193 - 61199
(2015/02/19)
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- Ionic liquid promoted synthesis of β-Enamino ketones and esters under microwave irradiation
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A facile amination of 1,3-dicarbonyl compounds with amines or ammonium salts has been achieved under microwave irradiation in the presence of acidic ionic liquid 1-butyl-3-methylimidazolium hydrogen sulphate. The method has the advantage of solvent free reactions, short reaction time and mild conditions.
- Singh, Ashima,Gupta, Neeru,Sharma,Singh, Jasvinder
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p. 900 - 906
(2014/08/05)
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- Chemical transformations of diazoles in the reactions of carboxylation, N-siloxycarbonylation, and transsilylation
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The behavior of 3,5-dimethylpyrazole, 3(5)-methylpyrazole, imidazole and their trimethyl-silyl derivatives in carboxylation, N-siloxycarbonylation, and transsilylation reactions was studied. A new Nsiloxycarbonylation reagent, diazole trimethylsilyl derivative-carbon dioxide, was found. This reagent makes it possible to obtain easily O-silylurethanes starting from primary, secondary amines and hydrazine derivatives, as well as to develop a convenient one pot synthesis method for trimethylsiloxycarbonyldiazoles.
- Belova,Pletnev,Kirilin
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p. 1365 - 1368
(2013/09/23)
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- Solid-state and solvent-free synthesis of azines, pyrazoles, and pyridazinones using solid hydrazine
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Azines, pyrazoles, and pyridazinones were isolated as the sole products in high yields (>97%) by grinding solid hydrazine (H3N +NHCO2-) with di-carbonyl compounds or by their reaction in the absence of solvent. Neither catalysts nor additives were needed to promote the reactions. The solid-state and solvent-free reactions proceeded under ambient conditions and did not produce any wastes other than water and carbon dioxide. They are operationally easy, environmentally safe, and readily scalable, allowing for highly selective synthesis of compounds containing the hydrazine motif. Copyright
- Lee, Byeongno,Kang, Philjun,Lee, Kyu Hyung,Cho, Jaeheung,Nam, Wonwoo,Lee, Won Koo,Hur, Nam Hwi
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supporting information
p. 1384 - 1388
(2013/04/23)
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- PEG-SO3H as a mild, efficient and green catalytic system for the synthesis of pyrazole derivatives in aqueous medium
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A versatile, alternative and environmentally benign strategy for the synthesis of a series of pyrazoles has been successfully performed in water using PEG-SO3H as an acidic catalyst. The products are obtained in high yield from the one-pot reaction procedure involving dicarbonyl compounds and hydrazines/hydrazides. This new method totally avoids the use of organic acids and toxic or expensive solvents in this reaction. The catalyst is waste-free, easily prepared, and efficiently re-used.
- Nasseri,Alavi,Zakeri Nasab
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p. 213 - 219
(2013/07/26)
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- Hydrotrope: Green and rapid approach for the catalyst-free synthesis of pyrazole derivatives
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An efficient synthesis of pyrazole derivatives by condensation of 1,3-diketone and hydrazines/hydrazides has been achieved in aqueous hydrotropic solution under catalyst-free conditions within a very short time. The present protocol is beneficial as it includes mild reaction conditions, shorter reaction times, use of universal solvent water, which avoids volatile organic solvents, high yields of products, and being environmentally friendly.
- Barge, Madhuri,Kamble, Santosh,Kumbhar, Arjun,Rashinkar, Gajanan,Salunkhe, Rajashri
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p. 1213 - 1218
(2013/08/23)
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- Nucleic acid interaction and antibacterial behaviours of a ternary palladium(II) complexes
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The bidentate ligands and Pd(II) complexes have been synthesized and characterized using elemental analysis (C, H, N), 1H NMR, 13C NMR, electronic spectra, FT-IR and FAB mass spectroscopy. The binding of palladium complexes with calf thymus DNA (CT DNA) has been explored using absorption titration, DNA melting temperature and viscosity measurements. The cleavage reaction on pUC19 DNA has been monitored by agarose gel electrophoresis. The results suggest that complexes can bind to DNA by intercalative modes and exhibit nuclease activities in which supercoil form is converted to open circular form. The antibacterial activity of ligands and complexes has been performed against three Gram(-ve) and two Gram(+ve) microorganisms and the study indicates that all the complexes show better microbial inhibition activity than ligands and palladium salt.
- Patel, Mohan N.,Dosi, Promise A.,Bhatt, Bhupesh S.
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experimental part
p. 508 - 514
(2012/02/05)
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- Dinickel(ii) complexes: Preparation and catalytic activity
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Ligands (La-c) based on 2,7-bis(3,5-di-R-pyrazol-1-yl)-1,8- naphthyridine (a, R = H; b, R = CH3; c, R = Ph) were prepared for the construction of a series of dinickel complexes. Treatment of Lx with NiCl2 in an anhydrous methanol/THF solution resulted in the formation of dinuclear complexes [(Lx)(μ-Cl)2Ni 2Cl2(CH3OH)2] (3, x = a; 4, x = b; 5, x = c). These new complexes were characterized by elemental analysis, IR and UV-Vis spectroscopic techniques. The structures of complexes 3 and 4 were further confirmed by X-ray diffraction studies. Interestingly, crystals of 4 were obtained as a co-crystallization of 4 and the methanol substituted species [{(Lb)(μ-Cl)2Ni2Cl(CH3OH) 3}Cl] (4′). These dinickel complexes have been tested in the catalytic homo-coupling of terminal alkynes with the use O2 as the oxidant, showing excellent activities. A clear improvement on the catalytic activity of these complexes is observed as compared to the mono-nuclear species. The Royal Society of Chemistry 2012.
- Cheng, Ting-Peng,Liao, Bei-Sih,Liu, Yi-Hung,Peng, Shie-Ming,Liu, Shiuh-Tzung
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body text
p. 3468 - 3473
(2012/05/05)
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- Synthesis and enzyme inhibitory activities of some new pyrazole-based heterocyclic compounds
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Three tridentate N,N-bis(3,5-dimethylpyrazol- 1-ylmethyl)-1-hydroxy-2- aminoethane (2), N,N-bis(3,5-dimethylpyrazol- 1-ylmethyl)-cyclohexylamine (3) and 2-[bis (1,5-dimethyl-1H-pyrazol-3-ylmethyl)amino]ethan-1-ol (4) are synthesized and spectroscopically characterized togetherwith 1-hydroxymethyl-3,5-dimethylpyrazole (1). These have been tested in inhibitory activities against various hyperactive enzymes like urease, β- glucuronidase, phosphodiesterase, α-chymotrypsin, acetylcholinesterase and butyrylcholinesterase. Compounds 1, 2 and 3 were found to be selective inhibitors of urease. Compound 4 was found to be selective inhibitor of butyrylcholinesterase. The nature of the junction between pyrazoles cycles determined the activities of these tripods. While the tripods are inactive towards urease or glucuronidase, they turn to be selective towards butyrylcholinesterase.
- Harit, Tariq,Malek, Fouad,Bali, Brahim El,Khan, Ajmal,Dalvandi, Kourosh,Marasini, Bishnu P.,Noreen, Shagufta,Malik, Rizwana,Choudhary, M. Iqbal,Khan, Sadia
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p. 2772 - 2778,7
(2020/08/24)
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- Synthesis of [1,2,4]triazolo[4,3-b]-s-tetrazines with incorporated furazan ring
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Furazancarboxylic hydrazides can serve as nucleophiles to substitute for one dimethylpyrazole fragment in bis(3,5-dimethylpyrazol-1-yl)-s-tetrazine, giving the corresponding N-[6-(3,5-dimethylpyrazol-1-yl)-s-tetrazin-3-yl] -4-R-furazan-3-carbohydrazides i
- Sheremetev,Palysaeva,Suponitskii,Struchkova
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p. 121 - 130
(2013/01/15)
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- Reactivity of bis(3,5-dimethylpyrazol-1-yl)methyllithium with S or CS 2, followed by reaction with Fe3(CO)12 and Ar3SnCl or RX: Unexpected formation of (3,5-dimethylpyrazol-1-yl) dithioformate derivatives
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Reaction of bis(3,5-dimethylpyrazol-1-yl)methyllithium with sulfur at -70 °C, followed by reaction with Fe3(CO)12 and triaryltin chlorides, yielded trinuclear butterfly cluster complexes. When the triaryltin chlorides were replaced by organic halides, unexpected (3,5-dimethylpyrazol-1- yl)dithioformate derivatives were obtained. In addition, treatment of bis(3,5-dimethylpyrazol-1-yl)methane with n-BuLi at 0 °C resulted in partial decomposition to yield a carbene intermediate and a 3,5-dimethylpyrazolate anion. The carbene intermediate readily dimerized, and reaction of the anion with carbon disulfide, and subsequently with Fe3(CO)12 and organic halides, also gave the dithioformate derivatives.
- Liu, Xia-Li,Zhang, Xiao-Yan,Song, Hai-Bin,Tang, Liang-Fu
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experimental part
p. 5108 - 5113
(2012/09/05)
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- Zn[(l)proline]2 in water: A new easily accessible and recyclable catalytic system for the synthesis of pyrazoles
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Zn[(l)proline]2 has been found to be an efficient catalyst for the synthesis of pyrazole derivatives in pure water at room temperature. Reaction afforded moderate to excellent yield within a lesser time. Various pyrazoles which could not be prepared by other methods can be easily prepared by this method efficiently. Catalyst exhibits recyclability up to five runs. Hence our present protocol is economical and clean comprise of green reagent, solvent and catalyst.
- Kidwai, Mazaahir,Jain, Arti,Poddar, Roona
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experimental part
p. 1939 - 1944
(2011/06/19)
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- Synthesis, dimeric crystal structure, and fungicidal activity of 1-(4-methylphenyl)-2-(5-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)-4-phenyl-4H-1,2, 4-triazol-3-ylthio)ethanone
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A new triazole compound, C46H46N10O 2S2, has been synthesized, and the crystal structure was determined by a single crystal X-ray diffraction study. The fungicidal activity of the title compound was determined, and the results showed that it displays moderate fungicidal activity. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
- Liu, Xing-Hai,Tan, Cheng-Xia,Weng, Jian-Quan
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experimental part
p. 558 - 564
(2011/05/15)
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- Nitrogen-containing heterocycles from metal β-diketonates
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Factors determining the reaction of metal β-diketonates with hydrazine, in particular the nature of central metal ion and structure of β-diketonate ligand, are discussed. The possibility for the preparation of other heterocyclic compounds via reaction of metal acetylacetonates with phenylhydrazine, o-phenylenediamine, urea, and thiourea was studied.
- Svistunova,Shapkin,Nikolaeva,Apanasenko
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experimental part
p. 756 - 761
(2011/08/06)
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- A novel, broad-spectrum anticancer compound containing the imidazo[4,5-e][1,3]diazepine ring system
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Synthesis and broad-spectrum anticancer activity of a novel heterocyclic compound 1 containing the title imidazo[4,5-e][1,3]diazepine ring system have been reported. The compound shows potent in vitro antitumor activity with low micromolar IC50's against prostate, lung, breast, and ovarian cancer cell lines tested. The long alkyl chain attached to the six-position of the heterocyclic ring of 1 appears to be necessary for the observed biological activity.
- Xie, Min,Ujjinamatada, Ravi K.,Sadowska, Mariola,Lapidus, Rena G.,Edelman, Martin J.,Hosmane, Ramachandra S.
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experimental part
p. 4386 - 4389
(2010/10/01)
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- Reductive amine deallyl- and debenzylation with alkali metal in Silica Gel (M-SG)
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Alkali metals in silica gel (the M-SG materials) are effective reagents for reductive deallylation, debenzylation, debenzhydrylation, and detritylation of amines. As such, these reagents provide a convenient alternative to traditional metal ammonia solutions for this class of deprotections.
- Nandi, Partha,Dye, James L.,Jackson, James E.
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supporting information; experimental part
p. 3864 - 3866
(2009/09/28)
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- Room-temperature synthesis of pyrazoles, diazepines, β-enaminones, and β-enamino esters using silica-supported sulfuric acid as a reusable catalyst under solvent-free conditions
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Silica-supported sulfuric acid (H2SO4·SiO2) has been utilized as a heterogeneous recyclable catalyst for a highly efficient regio- and chemoselective condensation of hydrazines/hydrazides, diamines, and primary amines with various β-dicarbonyl compounds at room temperature to afford pyrazoles, diazepines, and β-enaminones/β-enamino esters under solvent-free conditions within 5-15 min. Copyright Taylor & Francis Group, LLC.
- Chen, Xiang,She, Jin,Shang, Zhi-Cai,Wu, Jun,Zhang, Peizhi
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experimental part
p. 947 - 957
(2009/09/06)
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- Facile synthesis and biological evaluation of some ethoxyphthalimide derivatives of pyrazolylthiazoloisoxazoles and pyrazolylthiadiazoles
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Reaction of acetylacetone with hydrazine hydrate gave 3,5-dimethyl-1H- pyrazole (1) which when reacted with ethylchloroacetate in acetone and thiosemicarbazide yielded ethyl-3,5-dimethyl-1H-pyrazol-17-yl-acetate (2) and 2-[(3,5-dimethyl-1H-pyrazol-1-yl)acetyl]hydrazine carbothioamide (3) respectively. Compound 3 acted as a key intermediate for both the series of final compounds. In one pathway, it was converted to corresponding thiadiazole (11) by treatment with conc. H2SO4 and NH3 which on condensation with ω-bromoethoxyphthalimide (10) gave 5-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-N-ethoxyphthalimido-1,3, 4-thiadiazol-2-amine (12). In another pathway, 3 reacted with chloroacetic acid to furnish 2-[(3,5-dimethyl-1H-pyrazolyl)-4-oxo-1,3-thiazolidin-2-ylidene acetohydrazide (4). Reaction of 4 with various araldehydes (5a-d) gave 5-[(4-substituted phenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]-2-[(3,5- dimethyl-1H-pyrazolyl)acetohydrazide (6a-d) which were further treated in two alternate routes. Firstly, with 10 to yield 5-{[(4-substituted phenyl)methylidene]-3-N-ethoxyphthalimido-4-oxo-1,3-thiazolidin-2-ylidene}-2-(3, 5-dimethyl-1H-pyrazolyl)acetohydrazide (8a-d). Cyclisation of these derivatives using hydroxylamine hydrochloride produced the target compounds 3-(4-substituted phenyl)-6-N-ethoxyphthalimido-3,3a-dihydro[1,3]thiazolo[4,5-c]isoxazol-5(6H)- ylidene-2-(3,5-dimethyl-1H-pyrazol-1-yl)acetohydrazide (9a-d). In parallel, 6a-d were first cyclised with hydroxylamine hydrochloride to give 3-[(4-substituted phenyl)-3,3a-dihydro[1,3]thiazolo[4,5-c]isoxazol-5(6H)-ylidene-2-(3, 5-dimethyl-1H-pyrazol-1-yl)acetohydrazide (7a-d) and then condensed with 10 to yield the final compounds 9a-d. Structural elucidation of synthesized compounds was accomplished by IR, 1H NMR, 13C NMR and mass spectral data. Final compounds were screened for their antimicrobial activity.
- Thadhaney, Bhawana,Sharma, Shweta,Sharma, Chirag,Talesara
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experimental part
p. 1204 - 1213
(2010/08/05)
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- Synthesis and biological activities of novel bis-heterocyclic pyrrodiazole derivatives
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Novel structures of bis-heterocyclic pyrrodiazole derivatives containing pyrazole were designed and synthesized. The title compounds were characterized by 1H NMR, IR, MS, and elemental analysis. Biological activities of three intermediate compounds and 25 pyrrodiazole derivatives were tested in vivo and in vitro. Some of the title compounds exhibited certain herbicidal activities against barnyardgrass and rape.
- He, Feng-Qi,Liu, Xing-Hai,Wang, Bao-Lei,Li, Zheng-Ming
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