15054-54-3Relevant articles and documents
Catalyst-free solventless synthesis of polysubstituted urea Method for preparing thioureas and chiral ureas and thiourea compounds
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Paragraph 0056-0062; 0084-0090, (2021/09/29)
The invention discloses a method for synthesizing polysubstituted urea, thiourea and chiral urea and thiourea compounds without catalyst without solvent, and the method comprises A contact reaction of an amine compound with a structure shown B as shown first in a non-catalyst and a solventless condition to prepare a polysubstituted urea or thiourea compound with a structure as shown C. R1 And R2 Each independently selected from a hydrocarbyl or substituted hydrocarbyl group, R3 The method is selected from H, hydrocarbyl or substituted hydrocarbyl, X is S or o. The method solves the defect that a catalyst and/or a solvent need to be used in the synthesis of urea and thiourea compounds in the prior art.
Hydroamination and Hydrophosphination of Isocyanates/Isothiocyanates under Catalyst-Free Conditions
Zhu, Xiancui,Xu, Mengchen,Sun, Jinrong,Guo, Dianjun,Zhang, Yiwei,Zhou, Shuangliu,Wang, Shaowu
, p. 5213 - 5218 (2021/10/19)
Symmetrical and unsymmetrical N,N’-disubstituted as well as trisubstituted ureas/thioureas by the hydroamination of isocyanates/isothiocyanates, and various phosphathioureas by the hydrophosphination of isothiocyanates have been synthesized in good to excellent yields under catalyst-free and mild conditions. This protocol is also applicable for the efficient synthesis of chiral ureas and thioureas and common herbicides, such as fenuron and monuron.
A Cu-Promoted C-N Coupling of Boron Esters and Diaziridinone: An Approach to Aryl Ureas
Li, Jing,Wang, Xiaoyu,Wang, Zhanwei,Shi, Yian
, p. 8958 - 8962 (2021/11/24)
A novel Cu-promoted C-N coupling between boron esters and di-tert-butyldiaziridinone is described. A wide variety of aryl ureas can be readily obtained under mild conditions with up to a 92% yield.
Electrochemical Synthesis of Carbodiimides via Metal/Oxidant-Free Oxidative Cross-Coupling of Amines and Isocyanides
Badsara, Satpal Singh,Jaiswal, Pradeep K.,Malviya, Bhanwar Kumar,Sharma, Siddharth,Verma, Ved Prakash
supporting information, (2020/03/19)
This work discloses an electrochemical oxidative cross-coupling of amines with aryl and aliphatic isocyanides. In an undivided cell, the reaction proceeds without involving any transition-metal catalyst, oxidant, or toxic reagents providing carbodiimides in good yields, thereby circumventing stoichiometric chemical oxidants, with H2 as the only byproduct. Moreover, carbodiimides were in situ converted into unsymmetrical ureas in moderate to good yields using an electricity ON-OFF strategy.
A Fe3O4?SiO2/Schiff Base/Pd Complex as an Efficient Heterogeneous and Recyclable Nanocatalyst for One-Pot Domino Synthesis of Carbamates and Unsymmetrical Ureas
Inaloo, Iman Dindarloo,Majnooni, Sahar
, p. 6359 - 6368 (2019/11/05)
A palladium-catalyzed domino method for the direct synthesis of carbamates and ureas has been developed by using readily available and economical starting materials (aryl halide, carbon monoxide, sodium azide, amines and alcohols) in a one-pot approach. The domino process underwent carbonylation, Curtius rearrangement, and nucleophilic addition. This protocol provides a step-economical and highly efficient reaction to access the wide range of valuable carbamates, symmetrical and unsymmetrical ureas with high yields under remarkable mild reaction conditions that are important factors in pharmaceutical science, biochemistry and agricultural industries. Furthermore, the magnetically recoverable nanocatalyst (Fe3O4?SiO2/Pd(II)) can be conveniently and swiftly recycled using external magnet and reused at least for seven times without noticeable loss of its catalytic activity.
2-Picolylamino(diphenylphosphinoselenoic)amide supported zinc complexes: Efficient catalyst for insertion of N–H bond into carbodiimides, isocyanates, and isothiocyanate
Harinath, Adimulam,Bano, Kulsum,Ahmed, Shakil,Panda, Tarun K.
supporting information, p. 23 - 32 (2017/09/25)
We report here the hydroamination of heterocumulenes such as carbodiimides, isocyanates, and isothiocyanates by zinc complexes supported by the ligand 2-picolylamino-(diphenylphosphinoselenoic)amide [{(Ph2P-(?Se)}2NCH2(C5H4N)] (1). A series of zinc complexes [κ2-{(Ph2P-(?Se)}2NCH2(C5H4N)ZnX2] [(X?Cl (2), Br (3a), I (4)] were prepared from ligand 1 and the corresponding zinc dihalide in a 1:1 molar ratio at 60°C in a chloroform solvent. The reaction of ligand 1 and ZnBr2 in methanol yielded another zinc complex [κ2-{(Ph2P-(?Se)}2NCH2(C5H4N)ZnBr2(CH3OH)] (3b). The molecular structures of compounds 3a, 3b, and 4 were established through single-crystal X-ray diffraction analyses. The solid-state structures of all the complexes revealed a κ2- chelation through pyridine nitrogen and selenium atoms of ligand 1 to the zinc ion. Complex 2 proved to be a competent pre-catalyst for the addition of the amine N–H bond to carbodiimides, isocyanates, and isothiocyanates. The reaction scope was expanded to reactions of aliphatic and aromatic amines with phenylisocyanate and phenylisothiocyanate in toluene solvents, which proceeded rapidly at room temperature with 5 mol% catalyst loading to yield (up to 99%) the corresponding derivatives of urea and thio-urea. However, a temperature of 90°C was needed for the hydroamination of N,N′ dicyclohexylcarbodiimide. We also report the most plausible mechanism of the hydroamination reaction.
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.
Oximes as reusable templates for the synthesis of ureas and carbamates by an: In situ generation of carbamoyl oximes
Senadi, Gopal Chandru,Mutra, Mohana Reddy,Lu, Ting-Yi,Wang, Jeh-Jeng
supporting information, p. 4272 - 4277 (2017/09/28)
Oximes have been identified as reusable templates for the synthesis of ureas and carbamates by an in situ generation of carbamoyl oximes under metal-free conditions. The recovered oxime has been utilised for three trials in the synthesis of urea derivatives without any loss in the yield and efficiency. In addition, this template approach could override the usage of hazardous and less stable isocyanates as substrates.
Amine Activation: N-Arylamino Acid Amide Synthesis from Isothioureas and Amino Acids
Zhu, Yan-Ping,Mampuys, Pieter,Sergeyev, Sergey,Ballet, Steven,Maes, Bert U. W.
, p. 2481 - 2498 (2017/07/22)
N-arylamino acid amides have been synthesized via a novel method based on N-arylamine activation into isothioureas followed by reaction with amino acids under iron catalysis. The activated N-arylamines are easily prepared using a three-component reaction with commercial reagents, tert-butylisocyanide and S-phenyl benzenethiosulfonate. The protocol shows a broad functional group compatibility, with respect to side chain functionality of the amino acid (e. g. aliphatic and aromatic OH, (hetero)aromatic NH, amide NH, thioether), and the chiral amino acids do not undergo epimerization. The mechanism of the new amide synthesis has been studied. (Figure presented.).
Synthesis and SAR studies of potent H+/K+-ATPase and anti-inflammatory activities of symmetrical and unsymmetrical urea analogues
Rakesh, Kadalipura P.,Darshini, Nanjudappa,Vidhya, Sunnadadoddi L.,Rajesha,Mallesha, Ningegowda
, p. 1675 - 1681 (2017/06/27)
A sequence of symmetrical and unsymmetrical urea derivatives 1–24 were synthesized and characterized by standard spectroscopic techniques. The synthesized analogues were tested for their in vitro H+/K+-ATPase and anti-inflammatory activities. The majority of the compounds showed outstanding activity, compared to that of omeprazole and indomethacin, usual standard drugs of antiulcer and anti-inflammatory, respectively. In particular, hydroxy, methyl, and methoxy derivatives 13–24 were the most active compounds possessing a significant amplify for diverse substituents on the benzene ring thus, contributing positively to gastric ulcer inhibition. Compounds 1–3 and 22–24 showed excellent anti-inflammatory activity due to the presence of electron-withdrawing groups (Cl and F) on the molecule.
