20518-17-6

Usage

Synthesis Reference(s)

Tetrahedron Letters, 33, p. 659, 1992 DOI: 10.1016/S0040-4039(00)92336-0

InChI:InChI=1/C10H10N2/c1-9-3-5-10(6-4-9)12-8-2-7-11-12/h2-8H,1H3

Upstream product

• 88254-47-1 (E)-1-(4-tolyl)-2-((E)-3-phenylallylidene)hydrazone 
• 23768-90-3 1,5-di-p-tolyl-1,5-diazapenta-1,3-diene 
• 52913-14-1 O-tosylhydroxylamine 
• 288-13-1 NH-pyrazole 
• 624-31-7 4-tolyl iodide 
• 102-52-3 malonaldehydebis(dimethylacetal) 
• 539-44-6 N-4-methylphenylhydrazine 
• 106-49-0 p-toluidine 
• 99-99-0 1-methyl-4-nitrobenzene 
• 352-32-9 p-fluorotoluene 
• 29540-83-8 p-tolyl triflate 
• 108-88-3 toluene 
• 637-60-5 p-tolylhydrazine hydrochloride 
• 106-43-4 para-chlorotoluene 

Downstream Products

• 13910-54-8 N¹-(4-methylphenyl)propane-1,3-diamine 
• 861161-82-2 2-methyl-1-[1-(4-methylphenyl)-1H-pyrazol-5-yl]propan-1-ol 
• 110108-58-2 (5-methyl-2-(1H-pyrazol-1-yl)phenyl)(phenyl)methanone 
• 1190991-80-0 5-methyl-2-(1H-pyrazol-1-yl)benzonitrile 
• 1260140-70-2 4,5-diphenyl-7-methylpyrazolo[1,5-a]quinoline 
• 84401-18-3 1-(2,4-dimethylphenyl)-(1H-pyrazole) 
• 1214622-46-4 5-methyl-2-(1H-pyrazol-1-yl)benzoic acid 
• 1262659-71-1 2-(1H-pyrazol-1-yl)-1,3-benzendicarboxylic acid 1,3-dimethyl ester 
• 1262659-74-4 5-methyl-2-(1H-pyrazol-1-yl)-1,3-benzendicarboxylic acid 1,3-dimethyl ester 
• 1352633-02-3 1-{2-[(E)-2-(n-butoxycarbonyl)ethenyl]-4-methylphenyl}-1H-pyrazole 
• 1352633-04-5 1-{2,6-bis[(E)-2-(n-butoxycarbonyl)ethenyl]-4-methylphenyl}-1H-pyrazole 
• 1417034-40-2 1-[2,6-bis[(1E)-1,2-diphenylethenyl]-4-methylphenyl]pyrazole 
• 337957-59-2 1-(4-methylphenyl)-1H-pyrazole-4-carbaldehyde 
• 1444302-84-4 C₁₀H₉FN₂ 

Relevant academic research and scientific papers

N-ARYLATION OF AZOLES AND THEIR BENZO DERIVATIVES BY p-TOLYLLEAD TRIACETATE

The N-arylation of a variety of azoles and their benzo derivatives was achieved by treatment at 90-100 deg c with p-tolyllead triacetate in the presence of copper (II) acetate.

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

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.

A post-synthetically modified metal-organic framework for copper catalyzed denitrative C-N coupling of nitroarenes under heterogeneous conditions

Here we report, for the first time, the Ullmann C-N coupling reaction of nitroarenes which is achieved by using a copper containing metal-organic framework (MOF) catalyst under heterogenous conditions. The ready availability of nitroarenes and their low cost have made them ideal replacements for haloarenes as electrophilic coupling partners. Notably, the reaction protocol suppresses the by-product formation in the catalytic reaction. The catalyst has been designed and synthesized by two step post-synthesis functionalization of a MOF,viz.dabco MOF-1 with a -NH2functional group (DMOF-NH2). In the post-synthetic treatment, salicylaldehyde has been used for organic modification first and then copper(ii) was successfully incorporated onto the inner surface of the porous material. The hybrid porous solid thus obtained has been employed in the catalytic C-N coupling reaction of nitroarenes with a wide variety of amines under heterogeneous conditions, which displayed very high turnover frequencies (TOF) in catalytic reactions attesting its efficacy towards theN-arylation reaction.

2 - Alkynyl mannose derivative and application thereof

The present invention relates to a 2-alkynyl mannose derivative and an application thereof. The mannose derivative, as well as a pharmaceutically acceptable salt, an isotope and an isomer thereof have the structure represented by general formula I. The de

Copper pyrithione (CuPT)-catalyzed/mediated amination and thioarylation of (hetero)aryl halides: A competition

A facile method for the synthesis of N-arylheterocycles and di(hetero)aryl sulfides under mild condition is described. In these transformations, copper pyrithione (CuPT) was used as the copper catalyst for C─N coupling, while served as catalyst and coupled partner for C─S coupling with high yields and broad substrate tolerance. The S-arylation process was also utilized for the construction of valuable bioactive 2-sulfonylpyridine 1-oxide derivatives.

Copper quinolate: A simple and efficient catalytic complex for coupling reactions

We describe an effective and novel method to prepare N-aryl imidazoles via the copper quinolate-catalyzed N-arylation of aryl halides and imidazoles. A wide range of products were obtained in moderate to excellent yields under the optimal reaction conditions. Applying standard conditions, the model reaction could be performed on a gram scale. This method also presents a new avenue to the “click” reaction of terminal alkynes, benzyl bromide, and sodium azide and to the construction of C–C bonds by homocoupling of phenylboronic acid or phenylacetylene derivatives with the aid of copper quinolate.

Nucleophilic aromatic substitution of unactivated fluoroarenes enabled by organic photoredox catalysis

Nucleophilic aromatic substitution (SNAr) is a classical reaction with well-known reactivity toward electron-poor fluoroarenes. However, electron-neutral and electron-rich fluoro(hetero)arenes are considerably underrepresented. Herein, we present a method for the nucleophilic defluorination of unactivated fluoroarenes enabled by cation radical-accelerated nucleophilic aromatic substitution. The use of organic photoredox catalysis renders this method operationally simple under mild conditions and is amenable to various nucleophile classes, including azoles, amines, and carboxylic acids. Select fluorinated heterocycles can be functionalized using this method. In addition, the late-stage functionalization of pharmaceuticals is also presented. Computational studies demonstrate that the site selectivity of the reaction is dictated by arene electronics.

SUBSTITUTED PYRAZOLE DERIVATIVES AS INSECTICIDES AND FUNGICIDES

An object of the present disclosure is to provide a novel substituted pyrazole compound or a salt thereof as represented by formula (1) that controls pests: wherein, Q represents an oxygen atom or a sulfur atom, or the like; R represents substituted or unsubstituted aryl, C1-C12alkyl, or the like; Represents hydrogen, substituted or unsubstituted C1- C12alkylcarbonyl, substituted or unsubstituted C1-C12alkoxycarbonyl or the like; R2and R3each independently represent hydrogen, substituted or unsubstituted C1-C12alkyl, or the like; R4and R5each independently represent hydrogen, substituted or unsubstituted C1- C12alkyl, or the like; andX1, X2and X3grepresent C-R8, C-Rg and C-R|0, respectively, wherein R8, R9and Rjgeach independently represent hydrogen, halogen, methyl, ethyl or the like. The compounds of formula (1) are useful as insecticides and fungicides.

A Highly Active, Recyclable and Cost-Effective Magnetic Nanoparticles Supported Copper Catalyst for N-arylation Reaction

Abstract: The immobilization of a copper complex by covalent anchoring of 2-hydroxybenzophenone on the surface of amine-functionalized magnetic nanoparticles was reported. The structure and morphology of the catalyst was characterized by different techniques such as Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), transmission electron micrograph (TEM), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDS), vibrating sample magnetometer (VSM) and inductively coupled plasma (ICP) spectroscopy. This efficient and cost effective catalyst was applied in the N-arylation reaction and the products were obtained in good to excellent yields in short reaction times. The cost-effective catalyst demonstrated high stability, which could be facilely separated from the reaction mixture by applying an external magnet and recycled at least four times with only a slight decrease in its activity. Graphic Abstract: [Figure not available: see fulltext.]

Palladium-Catalyzed C-N Cross-Coupling of NH-Heteroarenes and Quaternary Ammonium Salts via C-N Bond Cleavage

In this paper, we extend the substrate class of Buchwald-Hartwig amination to quaternary ammonium salts. In the presence of Pd(OAc)2 and t-BuXPhos, the coupling of aryl- or arylmethyltrimethylammonium triflates with NH-heteroarenes via C-N bond cleavage affords the desired N-aryl or N-arylmethyl heteroarenes in moderate to excellent yields.