- Dual palladium-photoredox catalyzed chemoselective C-H arylation of phenylureas
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A highly chemoselective C-H arylation of phenylureas has been accomplished using dual palladium-photoredox catalysis at room temperature without any additives, base or external oxidants. Regioselective C-H arylation ofN,N'-diaryl substituted unsymmetrical phenylureas has also been accomplished by a careful choice of aryl groups.
- Babu, Sakamuri Sarath,Shahid,Gopinath, Purushothaman
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supporting information
p. 5985 - 5988
(2020/06/04)
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- Superparamagnetic Fe3O4 Nanoparticles in a Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Primary Carbamates and Monosubstituted Ureas
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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.
- Inaloo, Iman Dindarloo,Majnooni, Sahar,Esmaeilpour, Mohsen
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p. 3481 - 3488
(2018/07/29)
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- A practically simple, catalyst free and scalable synthesis of: N -substituted ureas in water
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A practically simple, mild and efficient method is developed for the synthesis of N-substituted ureas by nucleophilic addition of amines to potassium isocyanate in water without organic co-solvent. Using this methodology, a variety of N-substituted ureas (mono-, di- and cyclic-) were synthesized in good to excellent yields with high chemical purity by applying simple filtration or routine extraction procedures avoiding silica gel purification. The developed methodology was also found to be suitable for gram scale synthesis of molecules having commercial application in large volumes. The identified reaction conditions were found to promote a unique substrate selectivity from a mixture of two amines.
- Tiwari, Lata,Kumar, Varun,Kumar, Bhuvesh,Mahajan, Dinesh
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p. 21585 - 21595
(2018/06/26)
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- 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)
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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.
- Habibi, Davood,Heydari, Somayyeh,Faraji, Alireza,Keypour, Hasan,Mahmoudabadi, Masoumeh
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p. 520 - 529
(2018/06/26)
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- 4-Dodecylbenzenesulfonic acid (DBSA) promoted solvent-free diversity-oriented synthesis of primary carbamates, S-thiocarbamates and ureas
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A simple and highly efficient solvent-free method for the conversion of alcohols, phenols, thiols and amines to primary carbamates, S-thiocarbamates and ureas in the presence of 4-dodecylbenzenesulfonic acid (DBSA) as a cheap and green Bronsted acid reagent has been described. All products were obtained in good to excellent yields and characterized using FT-IR, 1H- and 13C-NMR, MS and CHNS techniques.
- Sardarian, Ali Reza,Inaloo, Iman Dindarloo
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p. 76626 - 76641
(2015/09/22)
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- Green synthesis, optical properties and catalytic activity of silver nanoparticles in the synthesis of N-monosubstituted ureas in water
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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.
- Nasrollahzadeh, Mahmoud,Babaei, Ferydon,Mohammad Sajadi,Ehsani, Ali
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p. 423 - 429
(2014/06/23)
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- Synthesis of N-arylureas in water and their N-arylation with aryl halides using copper nanoparticles loaded on natural Natrolite zeolite under ligand-free conditions
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A new method for the synthesis of N-arylureas and their N-arylation with aryl halides has been developed using copper nanoparticles supported on natural Natrolite zeolite as a reusable heterogeneous catalyst under ligand-free conditions.
- Nasrollahzadeh, Mahmoud,Enayati, Mojtaba,Khalaj, Mehdi
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p. 26264 - 26270
(2014/07/08)
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- Nano cerium oxide as a recyclable catalyst for the synthesis of N-monosubstituted ureas with the aid of acetaldoxime as an effective water surrogate
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A new method for the synthesis of N-monosubstituted ureas has been developed by the reaction of cyanamides with acetaldoxime in the presence of nano cerium oxide as an efficient and recyclable catalyst.
- Sajadi, S. Mohammad,Maham, Mehdi
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p. 623 - 625
(2013/11/06)
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- Synthesis and anticonvulsant activity of halo-substituted aryl urea and thioureas
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Halo-substituted arylureas have been prepared by condensation of halo-substituted primary arylamine with sodium cyanate and halo-substituted arylthioureas have been prepared by condensation of halo-substituted primary arylamine with ammonium thiocyanate in presence of acid. The structures of compounds synthesized have been confirmed by elemental analysis and spectral data. Their anticonvulsant activity was evaluated, p-bromophenyl urea and p-chlorophenyl and p-bromophenyl thioureas were found to be most active in the maximal electro shock (MES) test. p-Bromophenyl derivatives were found least neurotoxic in the rotorod test. The results were compared with standard drug phenytoin.
- Gupta, Mahesh Kumar,Pandeya, Suerendra N.,Zaiad, Golal M.,Gangwar
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experimental part
p. 1421 - 1424
(2011/09/20)
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- Synthesis of novel aryl semicarbazones as anticonvulsants with GABA-mediated mechanism
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A series of 3-bromophenyl semicarbazone derivatives were synthesized and evaluated for anticonvulsant activity. Compound 5e demonstrated to have anticonvulsant activity in the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole seizure
- Yogeeswari, Perumal,Sriram, Dharmarajan,Brahmandam, Archana,Sridharan, Induja,Thirumurugan, Rathinasabapathy,Stables, James P.
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