13142-82-0Relevant academic research and scientific papers
N -Acylbenzotriazoles as Proficient Substrates for an Easy Access to Ureas, Acylureas, Carbamates, and Thiocarbamates via Curtius Rearrangement Using Diphenylphosphoryl Azide (DPPA) as Azide Donor
Yadav, Mangal S.,Singh, Sumt K.,Agrahari, Anand K.,Singh, Anoop S.,Tiwari, Vinod K.
, p. 2494 - 2502 (2021/03/26)
A diverse range of ureas, N -acylureas, carbamates, and thiocarbamates has been synthesized in good to excellent yields by reacting N -acylbenzotriazoles individually with amines or amides or phenols or thiols in the presence of diphenylphosphoryl azide (DPPA) as a suitable azide donor in anhydrous toluene at 110 °C for 3-4 hours. In this route, DPPA was found to be a good alternative to trimethylsilyl azide and sodium azide for the azide donor in Curtius degradation. The high reaction yields, one-pot and metal-free conditions, straightforward nature, easy handling, use of readily available reagents, and in many cases avoidance of column chromatography are the notable features of the devised protocol.
Synthetic method and application of urea compound
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Paragraph 0027-0029; 0031, (2019/06/07)
The invention relates to a synthetic method of a urea compound, comprising the following steps: adding substituted oxazolone and sodium acetate into a methanol solution, and adding substituted amine under the stirring condition, reacting and carrying out column chromatography to obtain the urea compound. The defect that dangerous compounds need to be used during existing synthetic process is overcome, and a one-pot method is adopted to replace an existing reaction with low yield. The method of the invention has mild reaction condition, the operation is simple, raw materials are easily available, and the substrate can be converted into various other useful molecules. The compound has strong practicality, and can be applied to synthesis of the pesticide daimuron, dieresis long and the anti-cancer drug Sorafenib. The invention relates to a green and environmentally-friendly unsymmetrical urea compound synthesis method with simple process and low cost.
An Improved Synthesis of Urea Derivatives from N -Acylbenzotriazole via Curtius Rearrangement
Agrahari, Anand K.,Singh, Anoop S.,Singh, Sumit K.,Tiwari, Vinod K.,Yadav, Mangal S.
, p. 3443 - 3450 (2019/09/07)
The good leaving tendency of the benzotriazole moiety has been exploited for the synthesis of symmetric, unsymmetric, N -acyl, and cyclic ureas in good yields from N -acylbenzotriazoles by treating the latter with various amines in the presence of TMSN 3 /Et 3 N in a sealed tube. The salient features of the devised protocol includes the high-yield, mild, metal-free, one-pot reaction conditions, and short reaction time. Furthermore, in many cases, no column chromatography is required for the purification.
An efficient synthesis of nitrile, tetrazole and urea from carbonyl compounds
Sribalan, Rajendran,Sangili, Arumugam,Banuppriya, Govindharasu,Padmini, Vediappen
, p. 3414 - 3421 (2017/07/13)
An efficient conversion of carbonyl compounds (aldehydes and ketones) to nitrile, tetrazole, and urea was developed with the use of a POCl3 and sodium azide mixture using a convergent and microwave method. This is the first report on the direct conversion of ketone to urea. The synthesized compounds were characterized by 1H NMR, 13C NMR, mass and IR spectroscopies and were found to be in agreement with reported compounds.
Cu(acac)2-catalyzed N-arylations of phenylurea with aryl boronic acid
Gavade, Sandip,Balaskar, Ravi,Mane, Madhav,Pabrekar, Pramod N.,Mane, Dhananjay
experimental part, p. 1704 - 1714 (2012/05/05)
Cu(acac)2 activates aryl boronic acids for the reaction with NH2-phenylurea without additional ligand and heating. The procedure is simple, general, ligand-free, milder than the palladium-catalyzed arylation, and avoids the use of toxic phosphine ligands. Copyright Taylor & Francis Group, LLC.
An efficient method for the N-arylation of phenylurea via copper catalyzed amidation
Gavade, Sandip N.,Balaskar, Ravi S.,Mane, Madhav S.,Pabrekar, Pramod N.,Shingare, Murlidhar S.,Mane, Dhananjay V.
experimental part, p. 675 - 678 (2012/01/13)
The coupling reaction of phenylurea with different functionalized aryl halides in the presence of air stable CuI, N,N-dimethylethylenediamine as a ligand, and K3PO4 as a base gives symmetrical and unsymmetrical diarylureas in relatively high yields. This method is milder than the palladium catalyzed arylation and avoids the use of toxic phosphine ligands.
Microwave assisted, solvent- and ligand-free copper catalyzed N-arylation of phenylurea with aryl halides
Gavade, Sandip,Shingare, Murlidhar,Mane, Dhananjay
experimental part, p. 4167 - 4170 (2012/02/16)
An inexpensive and efficient catalyst system has been developed for the N-arylation of phenylurea including a variety of aryl halides. This simple protocol uses Cu2O as the catalyst, microwave assisted, solvent- and ligand-free, K3PO4.H2O as the base.
Microwave assisted, ligand free, copper catalyzed reaction of aryl halides with phenyl urea
Gavade, Sandip N.,Balaskar, Ravi S.,Mane, Madhav S.,Pabrekar, Pramod N.,Shingare, Murlidhar S.,Mane, Dhananjay V.
experimental part, p. 292 - 295 (2012/01/05)
The ligand free coupling reaction of phenyl urea with different functionalized aryl halides in the presence of air stable Cu2O and t-BuOK as a base gives symmetrical and unsymmetrical diarylureas in relatively high yields. This method is milder than the palladium catalyzed arylation and avoids the use of toxic phosphine ligand.
An efficient and mild protocol for the synthesis of unsymmetrical ureas in the absence of catalyst and additives
Hosseinzadeh, Rahman,Sarrafi, Yaghoub,Aghili, Nora
experimental part, p. 1171 - 1174 (2011/10/04)
A new practical method for the synthesis of unsymmetrical ureas was achieved by reaction of phenylurea with primary and secondary amines under neutral and mild condition in very good yields. The reaction took place in refluxing dioxane and does not require any catalyst or additives.
Synthesis and studies of a super-structured porphyrin derivative - A potential building block for CcO mimic models
Charalambidis, Georgios,Ladomenou, Kalliopi,Boitrel, Bernard,Coutsolelos, Athanassios G.
experimental part, p. 1263 - 1268 (2009/07/19)
A novel porphyrin complex that contains an Fe porphyrin linked to a tridentate ligand where a Cu ion could be coordinated was synthesized. The molecule also incorporated a tyrosine mimic attached to the porphyrin ring via a urea bond and was fully charact
