556-10-5Relevant academic research and scientific papers
Templated synthesis of copper(II) azacyclam complexes using urea as a locking fragment and their metal-enhanced binding tendencies towards anions
Boiocchi, Massimo,Fabbrizzi, Luigi,Garolfi, Mauro,Licchelli, Maurizio,Mosca, Lorenzo,Zanini, Cristina
, p. 11288 - 11297 (2009)
Copper(II) azacyclam complexes 32+ and 42+ were obtained through a metal-templated procedure involving the pertinent open-chain tetramine, formaldehyde and a phenylurea derivative as a locking fragment. Both metal complexes can estab
A Straightforward Synthesis of N-Substituted Ureas from Primary Amides
Franck, Xavier,Glachet, Thomas,Ibert, Quentin,Lohier, Jean-Fran?ois,Reboul, Vincent,Saraiva Rosa, Nathalie
, p. 2099 - 2105 (2020/07/13)
A direct and convenient method for the preparation of N-substituted ureas is achieved by treating primary amides with phenyliodine diacetate (PIDA) in the presence of an ammonia source (NH 3 or ammonium carbamate) in MeOH. The use of 2,2,2-trifluoroethanol (TFE) as the solvent increases the electrophilicity of the hypervalent iodine species and allows the synthesis of electron-poor carboxamides. This transformation involves a nucleophilic addition of ammonia on the isocyanate intermediate generated in situ by a Hofmann rearrangement of the starting amide.
Superparamagnetic Fe3O4 Nanoparticles in a Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Primary Carbamates and Monosubstituted Ureas
Inaloo, Iman Dindarloo,Majnooni, Sahar,Esmaeilpour, Mohsen
, p. 3481 - 3488 (2018/07/29)
Superparamagnetic Fe3O4 nanoparticles were used to synthesize various primary carbamates as well as monosubstituted and N,N-disubstituted ureas. This efficient phosgene-free process used urea as an eco-friendly carbonyl source in the presence of a biocompatible deep eutectic solvent (DES) to provide an inexpensive and attractive route that afforded the products in moderate to excellent yields. The employed DES serves both a catalytic role and as the green reaction medium. The magnetic nanocatalyst and DES can been reused several times without a significant loss of activity.
Design and synthesis of novel N-(4-(Pyridin-2-yloxy)benzylidene)-4-[4-(substituted)phenyl]semicarbazides as potential anticonvulsant agents
Singh, Prem,Tripathi, Laxmi
, p. 2193 - 2200 (2018/09/10)
A new series of N-(4-(pyridin-2-yloxy)benzylidene)-4-[4-(substituted)phenyl]semicarbazides (PSSD1-8) were designed and synthesized keeping in view the structural requirement of pharmacophore and evaluated for their possible anticonvulsant activity. All the derivatives were synthesized by the given scheme and reaction process was monitored by thin layer chromatography. The structure of synthesized derivatives was confirmed by FT-IR, 1H NMR, mass spectroscopy and elemental analysis. The anticonvulsant activity was established after intraperitoneal administration in MES and scMET seizure models. The most active compound of the series was 1-(4-(pyridin-2-yloxy)-benzylidene)-4-p-tolylsemicarbazide (PSSD5). A molecular docking study was carried out in order to assess the interaction and binding modes with target receptor/enzyme. Titled compounds were found to strongly bind to human gamma-aminobutyric acid receptor (GABAAR-β3). A computational study was also carried to predict the pharmacokinetic properties of the synthesized compounds.
Synthesis of Amides by Nucleophilic Substitution of Hydrogen in 3-Nitropyridine
Amangasieva,Borovlev,Demidov,Avakyan,Borovleva
, p. 867 - 872 (2018/07/31)
3-Nitropyridine reacted with nitrogen-centered carboxylic acid amide anions in anhydrous DMSO in the presence of K3Fe(CN)6 via oxidative nucleophilic substitution of hydrogen to give previously unknown N-(5-nitropyridin-2-yl) carboxa
A green and facile approach for the synthesis of N-monosubstituted ureas in water: Pd catalyzed reaction of arylcyanamides (an unexpected behavior of electron withdrawing groups)
Habibi, Davood,Heydari, Somayyeh,Faraji, Alireza,Keypour, Hasan,Mahmoudabadi, Masoumeh
, p. 520 - 529 (2018/06/26)
The Fe3O4 magnetic nano-particles were prepared, coated with tetraethyl orthosilicate (TEOS), functionalized with 3-chloropropyltrimethoxysilane (CPTMS), further functionalized with 2,2′-(piperazine-1,4-diylbis(methylene) dianiline (PDMD) and the corresponding Pd complex synthesized as a novel nano-magnetic heterogeneous catalyst (Fe3O4@SiO2@CPTMS@PDMD@Pd) to be used for the synthesis of various N-monosubstituted ureas in water. Also, in another attempt to see the effect of HCOOH, the hydration reaction of arylcyanamide was carried out in the presence of HCOOH (water + 98% HCOOH) which had two effects: it decreased the amount of the Pd catalyst from 40 to 30 mg, and the reaction condition was changed from the reflux condition to room temperature. Interestingly, the arylcyanamides with electron withdrawing groups influence the course of the reaction and need more reaction times for completion which is an unexpected behavior, probably due to the high electron density around the central carbon atom of the nitrile group.
Transition Metal-Free Carbazole Synthesis from Arylureas and Cyclohexanones
Wu, Jun,Xie, Yanjun,Chen, Xiangui,Deng, Guo-Jun
supporting information, p. 3206 - 3211 (2016/10/21)
An efficient strategy for carbazole synthesis from arylureas and cyclohexanones under transition metal-free conditions has been developed. The combined use of potassium iodide and iodine could significantly improve the reaction efficiency to provide 2,6-disubstituted 9-arylcarbazoles in moderate to good yields. In this kind of transformation, the whole carbazole moiety (except the nitrogen atom) comes from two equivalents of cyclohexanones. (Figure presented.).
Selective and facile oxidative desulfurization of thioureas and thiobarbituric acids with singlet molecular oxygen generated from trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane
Azarifar, Davood,Golbaghi, Maryam
, p. 1 - 13 (2016/02/12)
An efficient and facile procedure using trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane has been developed for oxidative desulfurization of thioureas and thiobarbituric acids. The reactions proceeded smoothly very fast under mild conditions in basic media at room temperature to afford the respective ureas in excellent yields. Simple procedure and work up, mild conditions, high yields, short reaction times, use of highly potent and non-toxic oxidant are the main merits of the present method.
One-Pot Synthesis of N-Monosubstituted Ureas from Nitriles via Tiemann Rearrangement
Wang, Chien-Hong,Hsieh, Tsung-Han,Lin, Chia-Chi,Yeh, Wen-Hsiung,Lin, Chih-An,Chien, Tun-Cheng
, p. 1823 - 1826 (2015/08/06)
Amidoximes, obtained from the reaction of nitriles with hydroxylamine, underwent Tiemann rearrangement in the presence of benzenesulfonyl chlorides (TsCl or o-NsCl) to form the N-substituted cyanamides. Subsequently, acidic hydrolysis of the cyanamides afforded the corresponding N-monosubstituted ureas. The synthesis of N-monosubstituted ureas from nitriles was accomplished by three steps in one pot, which provides a direct access to versatile N-monosubstituted urea derivatives from a wide variety of nitriles.
Green synthesis, optical properties and catalytic activity of silver nanoparticles in the synthesis of N-monosubstituted ureas in water
Nasrollahzadeh, Mahmoud,Babaei, Ferydon,Mohammad Sajadi,Ehsani, Ali
, p. 423 - 429 (2014/06/23)
We report the green synthesis of silver nanoparticles by using Euphorbia condylocarpa M. bieb root extract for the synthesis of N-monosubstituted ureas in water. UV-visible studies show the absorption band at 420 nm due to surface plasmon resonance (SPR) of the silver nanoparticles. This reveals the reduction of silver ions (Ag+) to silver (Ago) which indicates the formation of silver nanoparticles (Ag NPs). This method has the advantages of high yields, simple methodology and easy work up.
