611-92-7Relevant articles and documents
Palladium-catalyzed decarbonylative C–N coupling to convert arylcarbamoyl chlorides to urea derivatives
Fan, Aihong,Peng, Jinsong,Zhou, Dun,Li, Xiang,Chen, Chunxia
supporting information, p. 1 - 12 (2020/07/27)
This paper describes the development of a palladium-catalyzed decarbonylative C–N coupling reaction that transforms arylcarbamoyl chlorides into tetrasubstituted ureas under a nitrogen atmosphere. A broad range of functional groups are compatible with this reaction, and diverse urea derivatives can be obtained with good to high yields.
Heavily Substituted Atropisomeric Diarylamines by Unactivated Smiles Rearrangement of N-Aryl Anthranilamides
Costil, Romain,Dale, Harvey J. A.,Fey, Natalie,Whitcombe, George,Matlock, Johnathan V.,Clayden, Jonathan
supporting information, p. 12533 - 12537 (2017/09/13)
Diarylamines find use as metal ligands and as structural components of drug molecules, and are commonly made by metal-catalyzed C?N coupling. However, the limited tolerance to steric hindrance of these couplings restricts the synthetic availability of more substituted diarylamines. Here we report a remarkable variant of the Smiles rearrangement that employs readily accessible N-aryl anthranilamides as precursors to diarylamines. Conformational predisposition of the anthranilamide starting material brings the aryl rings into proximity and allows the rearrangement to take place despite the absence of electron-withdrawing substituents, and even with sterically encumbered doubly ortho-substituted substrates. Some of the diarylamine products are resolvable into atropisomeric enantiomers, and are the first simple diarylamines to display atropisomerism.
Crystal Engineering of N,N′-Diphenylurea Compounds Featuring Phenyl-Perfluorophenyl Interaction
Yamasaki, Ryu,Iida, Mana,Ito, Ai,Fukuda, Kazuo,Tanatani, Aya,Kagechika, Hiroyuki,Masu, Hyuma,Okamoto, Iwao
, p. 5858 - 5866 (2017/11/07)
Here, aiming to adopt the phenyl-perfluorophenyl interaction to regulate molecular alignment and arrangement for crystal engineering, we examined and compared in detail the crystal structures of N,N′-diphenylurea compounds 1-6. We found that phenyl-perfluorophenyl interaction greatly influenced the intermolecular arrangement in the crystal, and we were able to prepare a cocrystal of 1 and 2, in which the molecules were alternately arranged under the control of the phenyl-perfluorophenyl interaction. This arrangement was driven by the asymmetric geometry of the hydrogen bonds in the cocrystal (1·2), in which 2, bearing two perfluorophenyl groups, worked as a better hydrogen bond donor. In contrast, NH connected to the phenyl group in 3 proved to be a better hydrogen bond donor due to the intramolecular resonance effect. N,N′-Dimethylated derivatives, 4-6, existed in cis-cis form in the crystal. Antiparallel carbonyl-carbonyl arrangements were observed in 4 and 6, while an unexpected carbonyl-perfluorophenyl interaction was observed in the crystal of 5. These findings will be helpful in the design of diphenylurea-based functional molecules, especially for solid-state application.
Functional foldamers that target bacterial membranes: The effect of charge, amphiphilicity and conformation
Patil-Sen, Yogita,Dennison, Sarah R.,Snape, Timothy J.
, p. 4241 - 4245 (2016/08/23)
By varying the molecular charge, shape and amphiphilicity of a series of conformationally distinct diarylureas it is possible to control the levels of phospholipid membrane lysis using membranes composed of bacterial lipid extracts. From the data obtained, it appears as though the lysis activity observed is not due to charge, conformation or amphiphilicity in isolation, but that surface aggregation, H-bonding and other factors may also play a part. The work provides evidence that this class of foldamer possesses potential for optimisation into new antibacterial agents.
B(C6F5)3-catalyzed methylation of amines using CO2 as a C1 building block
Yang, Zhenzhen,Yu, Bo,Zhang, Hongye,Zhao, Yanfei,Ji, Guipeng,Ma, Zhishuang,Gao, Xiang,Liu, Zhimin
supporting information, p. 4189 - 4193 (2015/08/11)
B(C6F5)3 was proven to be an efficient metal-free catalyst for the methylation of amines using CO2 as a C1 building block in the presence of hydrosilanes under easy-handling conditions. A broad range of N-alkylanilines, dialkylamines and primary anilines all proceeded well under the catalytic conditions.
A novel ZrO2-SO42- supported palladium catalyst for syntheses of disubstituted ureas from amines by oxidative carbonylation
Shi, Feng,Deng, Youquan,SiMa, Tianlong,Yang, Hongzhou
, p. 2161 - 2163 (2007/10/03)
The syntheses of disubstituted ureas by carbonylation of a series of amines in the presence of a sulfate modified zirconia supported palladium catalyst was investigated at an initial total pressure of 4.0 MPa and 135°C. High conversions and yields were achieved for the synthesis of symmetric dialkylureas. This supported catalyst could also be easily separated and recovered after reaction.
An efficient new protocol for the formation of unsymmetrical Tri-and tetrasubstituted ureas
Batey, Robert A.,Santhakumar,Yoshina-Ishii, Chiaki,Taylor, Scott D.
, p. 6267 - 6270 (2007/10/03)
A new method for producing unsymmetrical, tetrasubstituted ureas from N, N'carbonyldiimidazole (CDI) is presented. Carbamoyl imidazolium salts are prepared from the reaction of CDI with a secondary amine, followed by alkylation with MeI. Secondary amines add with ease to imidazolium salts at room temperature to give unsymmetrical, tetrasubstituted ureas in excellent yields.
MACROHETEROCYCLES. XV. SYNTHESIS AND ION-SELECTIVE CHARACTERISTICS OF CYCLIC N,N'-DIALKYLUREAS
Bogat-skii, A. V.,Luk'yanenko, N. G.,Kirichenko, T. I.,Limich, V. V.,Karpenko, L. P.
, p. 89 - 95 (2007/10/02)
A convenient method is proposed for the production of cyclic N,N'-dialkylureas by the reaction of cyclic thioureas with alkyl halides in the presence of aqueous alkali and phase-transfer catalysts.It was established that the reaction takes place through the formation of isothioureas with subsequent alkylation of the nitrogen atoms and hydrolytic cleavage of the obtained N,N'-dialkylthiouronium salt.This method was used for the synthesis of macrocyclic N,N'-dimethylpolyoxyethyleneureas.The ion-selective characteristics of the obtained crown compounds were studied.
Carbamoylation using the CO-containing Copper Complex derived from Lithium N-methylanilide
Wakita, Yoshiaki,Kobayashi, Toshio,Maeda, Minoru,Kojima, Masaharu
, p. 3395 - 3398 (2007/10/02)
Lithium N-methylanilide, prepared from N-methylaniline and n-butyllithium, readily absorbed CO at atmospheric pressure in the presence of cuprous iodide to produce a CO-containing copper complex.Treatment of this complex with organic halides gave the corresponding amides in good yields.Keywords - carbonylation; carbamoylation; carbon monoxide; cuprous iodide; lithium N-methylanilide
