114-83-0Relevant articles and documents
A formal [3+2] cycloaddition reaction of: N -methylimidazole as a masked hydrogen cyanide: Access to 1,3-disubstitued-1 H -1,2,4-triazoles
Yavari, Issa,Khaledian, Omid
supporting information, p. 9150 - 9153 (2020/10/02)
N-Methylimidazole (NMI) can act as a masked HCN in the synthesis of 1,3-disubstitued-1H-1,2,4-triazoles via a formal cycloaddition reaction of hydrazonoyl chloride with NMI. The product was proved to be formed via an initial nucleophilic substitution of hydrazonoyl chloride with NMI following cyclization and two sequential C-N bond cleavages. This journal is
Synthesis of acetamides via oxidative C–C bond cleavage of ketones catalyzed by Cu-immobilized magnetic nanoparticles
Yazdani, Elahe,Pazoki, Farzane,Salamatmanesh, Arefe,Nejad, Masoume Jadidi,Miraki, Maryam Kazemi,Heydari, Akbar
, (2020/07/27)
Copper supported on magnetite nanoparticles modified with environmentally friendly ligand tricine was devised for synthesis of acetamides via C–C oxidative cleavage of ketones with amines. The catalyst was characterized using different techniques, including Fourier transform infrared, X-ray diffraction, scannin electron microscopy, vibrating sample magnetometry, thermogravimetric analysis, and energy dispersive x-ray spectroscopy. The protocol showed relatively high yields of acetamide products. Furthermore, the magnetic recovery of the catalyst rendered the overall process fast and efficient. It was used in the reaction for six consecutive cycles with negligible loss of catalytic activity. This research is the first report of application of magnetic nanocatalysts for synthesis of acetamides from ketones of low activity through a C–C bond cleavage strategy.
A magnetically recoverable copper–salen complex as a nano-catalytic system for amine protection via acetylation using thioacetic acid
Yazdani, Elahe,Kazemi Miraki, Maryam,Salamatmanesh, Arefe,Azarnia, Jamshid,Azizi, Kobra,Ghandi, Leila,Heydari, Akbar
, p. 1775 - 1793 (2019/01/16)
A novel copper(II)–salen complex was immobilized on the surface of magnetite nanoparticles using chitosan as a linker. This system exhibits superior catalytic activity in acetyl protection of various amines with thioacetic acid as the acetylating reagent. The method has advantages over others in high selectivity, simple work-up, green reaction medium and the application of an easily recoverable heterogeneous catalyst.
The impact of cation structure upon the acidity of triazolium salts in dimethyl sulfoxide
Konstandaras, Nicholas,Dunn, Michelle H.,Guerry, Max S.,Barnett, Christopher D.,Cole, Marcus L.,Harper, Jason B.
supporting information, p. 66 - 75 (2019/12/26)
A series of triazolium salts, selected for their varying electronic and steric properties, were prepared and their pKa values were determined in DMSO at 25 °C using the bracketing indicator method. The effect of each systematic structural variation upon the acidity of the triazolium cation has been considered, in particular examining the effects of systematically altering electronic properties, quantified through the use of Hammett σ parameters. The first pKa value for an azolium salt that generates a mesionic carbene is also reported. These new data allow for the selection of appropriate bases for the deprotonation of such triazolium salts and the potential to correlate the pKa values determined herein with the nucleophilicity of the corresponding carbenes.
Synthesis method for organic synthesis of intermediate acetyl phenylhydrazine
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Paragraph 0011; 0013; 0014; 0015, (2018/07/30)
The invention relates to a synthesis method for organic synthesis of an intermediate acetyl phenylhydrazine. The method mainly includes the steps of: adding 3mol phenylhydrazine into a reaction container and 4-5mol p-iodoacetanilide into a reaction container, performing heating to 90-95DEG C, conducting reflux for 130-150min, lowering temperature to 10-15DEG C, filtering the crystal, conducting washing with a methylamine solution and a dichloromethane solution respectively, performing recrystallization in an ethanol solution, precipitating crystals, conducting filtration, and performing dehydration with a dehydrating agent, thus obtaining the finished product acetyl phenylhydrazine.
Mild and eco-friendly chemoselective acylation of amines in aqueous medium using a green, superparamagnetic, recoverable nanocatalyst
Miraki, Maryam Kazemi,Yazdani, Elahe,Ghandi, Leila,Azizi, Kobra,Heydari, Akbar
, (2017/09/30)
Copper-grafted guanidine acetic acid-modified magnetite nanoparticles (Fe3O4@GAA-Cu(II)) as a green, superparamagnetic and recoverable nanocatalyst is found to promote quantitative N-acylation of various amines in a very short time with an equimolar amount of thioacetic acid in water at room temperature. This method is found to be highly selective for amines and not sensitive to other functional groups. Mild reaction condition, high selectivity, efficiency, simple workup and excellent yields are some of the major advantages of the procedure.
Palladium/copper-catalyzed arylation of alkenes with N′-acyl arylhydrazines
Zhang, Ji-Quan,Cao, Jun,Li, Wei,Li, Shu-Min,Li, Yong-Kang,Wang, Jian-Ta,Tang, Lei
supporting information, p. 437 - 441 (2017/02/05)
A novel ligand-free palladium/copper-catalyzed Heck-type coupling reaction of alkenes and N′-acyl arylhydrazines has been developed by using air as the terminal oxidant. This protocol features wide functional group tolerance and produces highly chemoselective and regioselective products with good to excellent yields.
[3+3]-cycloaddition of donor-acceptor cyclopropanes with nitrile imines generated in situ: Access to tetrahydropyridazines
Garve, Lennart K. B.,Petzold, Martin,Jones, Peter G.,Werz, Daniel B.
supporting information, p. 564 - 567 (2016/02/18)
Donor-acceptor cyclopropanes are reacted under the influence of a Lewis acid with hydrazonyl chlorides to afford tetrahydropyridazines. Formally, this transformation can be regarded as a [3 + 3]-cycloaddition of three-membered rings and nitrile imines generated in situ. This efficient method provides fast access to a variety of structurally diverse pyridazine derivatives. The structure of a typical product was confirmed by X-ray crystallography.
Microwave-assisted catalyst-free synthesis of substituted 1,2,4-triazoles
Shelke, Ganesh M.,Rao, V. Kameswara,Jha, Mukund,Cameron, T. Stan,Kumar, Anil
, p. 404 - 407 (2015/02/19)
A simple, efficient, and mild method has been developed for the synthesis of substituted 1,2,4-triazoles from hydrazines and formamide under microwave irradiation. The reaction proceeds smoothly in the absence of a catalyst and shows excellent functional-group tolerance.
Copper(ii)-catalyzed coupling reaction: An efficient and regioselective approach to N′,N′-diaryl acylhydrazines
Zhang, Ji-Quan,Huang, Gong-Bin,Weng, Jiang,Lu, Gui,Chan, Albert S. C.
supporting information, p. 2055 - 2063 (2015/03/05)
Using N′-aryl acylhydrazines as aryl donors, a novel copper(ii)-catalyzed homo-coupling reaction of N′-aryl acylhydrazines has been developed for the synthesis of N′,N′-diaryl acylhydrazines. We also provided a complementary procedure for the preparation of unsymmetrical diaryl acylhydrazines via cross-coupling reaction. These protocols featured mild reaction conditions, wide functional group tolerance and highly regioselective products. Control experiments indicated that this kind of coupling reaction might undergo a transient acyl diazene intermediate. This journal is
