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103-71-9Relevant articles and documents
CARBONYLATION OF NITROBENZENE WITH RUTHENIUM CLUSTERS
Basu, Amitabha,Bhaduri, Sumit,Khwaja, Hanif
, p. C28 - C30 (1987)
Evidence is presented for the participation of cluster intermediates in the carbonylation of nitrobenzene.
Carbamoyl complexes as a source of isocyanates or carbamyl chlorides
Giannoccaro, Potenzo,Tommasi, Immacolata,Aresta, Michele
, p. 13 - 18 (1994)
Isocyanates or carbamyl chlorides have been prepared by reaction of carbamoyl complexes of nickel and palladium with CuCl2.Isocyanates are selectively produced from the carbamoyl complexes of primary amines, , (L=2,6-bis(diphenylphosphinomethyl) pyridine; R=C6H5, p-CH3C6H4, or p-ClC6H4)) and , whereas carbamoyl complexes of secondary amines, such as , afford carbamyl chloride.As expected, the reaction of the resulting isocyanates or carbamyl chlorides in situ with alcohols or amines produces carbamates or N,N'-substituted ureas, respectively.Key words: Carbamyl chloride; Carbamate; Carboxamide; Chloroformamide; Complex; Isocyanates; Palladium; Phosphine; Synthesis
Preferred Binding of Carboxylates by Chiral Urea Derivatives Containing α-Phenylethyl Group
Cortés-Hernández, Mayra,Rojas-Lima, Susana,Hernández-Rodríguez, Marcos,Cruz-Borbolla, Julián,López-Ruiz, Heraclio
, p. 416 - 424 (2016)
An efficient, simple protocol for the synthesis of a new family of chiral ureas 1 – 4 is described. The binding properties of 1 – 4 toward different anion (acetate, benzoate, fluoride, and chloride) have been studied by1H-NMR titration and have been observed in the case of 4 is a selective receptor for acetate. The theoretical calculation M06/6-311+G(d,p) helped us explain the binding properties observed. The most interesting observation is that this calculated structure is consistent with expected, based on the concept of allylic 1,3-strain (A1,3strain). When chiral caboxylates were studied, urea 1 was the best in discriminating between enantiomers.
Design, Synthesis and Biological Evaluation of a New Series of 1-Aryl-3-{4-[(pyridin-2-ylmethyl)thio]phenyl}urea Derivatives as Antiproliferative Agents
Zhang, Chuanming,Tan, Xiaoyu,Feng, Jian,Ding, Ning,Li, Yongpeng,Jin, Zhe,Meng, Qingguo,Liu, Xiaoping,Hu, Chun
, (2019)
To discover new antiproliferative agents with high efficacy and selectivity, a new series of 1-aryl-3-{4-[(pyridin-2-ylmethyl)thio]phenyl}urea derivatives (7a–7t) were designed, synthesized and evaluated for their antiproliferative activity against A549, HCT-116 and PC-3 cancer cell lines in vitro. Most of the target compounds demonstrated significant antiproliferative effects on all the selective cancer cell lines. Among them, the target compound, 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-{4-{{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}thio}phenyl}urea (7i) was identified to be the most active one against three cell lines, which was more potent than the positive control with an IC50 value of 1.53 ± 0.46, 1.11 ± 0.34 and 1.98 ± 1.27 μM, respectively. Further cellular mechanism studies confirmed that compound 7i could induce the apoptosis of A549 cells in a concentration-dependent manner and elucidated compound 7i arrests cell cycle at G1 phase by flow cytometry analysis. Herein, the studies suggested that the 1-aryl-3-{4-[(pyridin-2-ylmethyl)thio]phenyl}urea skeleton might be regarded as new chemotypes for designing effective antiproliferative agents.
Multijet oscillating disc millireactor: A novel approach for continuous flow organic synthesis
Liguori, Lucia,Bjorsvik, Hans-Rene
, p. 997 - 1009 (2011)
This report discloses proof of concept and experimental results from a project involving design, development, and investigation of a novel approach for flow chemistry and the realization of equipment operating according to this new approach. This device is named multijet oscillating disk (MJOD) reactor and is dedicated to continuous flow organic synthesis in milliscale. Characteristics such as the importance of the multijet disk unit, with or without oscillating, and possible limitations, such as back-mixing, have been explored, and the flow system is benchmarked with other technologies. Several well-known reactions and syntheses usefully both in the chemical industry as well as in the research laboratory have been conducted using the new system, which have been benchmarked with batch- and microreactor protocols. In particular the Haloform reaction, the Nef reaction, nucleophilic aromatic substitution, the Paal-Knorr pyrrole synthesis, sodium borohydride reduction, O-allylation, the Suzuki cross-coupling reaction, the Hofmann rearrangement and N-acylation were performed during the study of the MJOD reactor performance. Our investigations revealed that the MJOD millireactor system can produce various organic compounds at a high rate concomitant with an excellent selectivity. A Hofmann rearrangement was conducted, a reaction that involves handling of a slurry of the substrate. This reaction was successfully conducted, achieving a quantitative conversion into the target molecule.
CO2 conversion to phenyl isocyanates by uranium(vi) bis(imido) complexes
Maria, Leonor,Bandeira, Nuno A. G.,Mar?alo, Joaquim,Santos, Isabel C.,Gibson, John K.
, p. 431 - 434 (2020)
Uranium(vi) trans-bis(imido) complexes [U(κ4-{(tBu2ArO)2Me2-cyclam})(NPh)(NPhR)] react with CO2 to eliminate phenyl isocyanates and afford uranium(vi) trans-[OUNR]2+ complexes, including [U(κ4-{(tBu2ArO)2Me2-cyclam})(NPh)(O)] that was crystallographically characterized. DFT studies indicate that the reaction proceeds by endergonic formation of a cycloaddition intermediate; the secondary reaction to form a dioxo uranyl complex is both thermodynamically and kinetically hindered.
The curtius rearrangement of acyl azides revisited - Formation of cyanate (R-O-CN)
Wentrup, Curt,Bornemann, Holger
, p. 4521 - 4524 (2005)
The Curtius rearrangement is a synthesis of isocyanates (R-N=C=O) by thermal or photochemical rearrangement of acyl acides and/or acylnitrenes. The photochemical rearrangement of benzoyl azide is now shown for the first time to produce a small amount of phenyl cyanate (Ph-O-CN) together with phenyl isocyanate. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Palladium-catalyzed reductive carbonylation of nitrobenzene for producing phenyl isocyanate
Nguyen, Thanh Tung,Tran, Anh Vy,Lee, Hye Jin,Baek, Jayeon,Kim, Yong Jin
, (2019)
Direct reductive carbonylation of nitrobenzene to phenyl isocyanate with carbon monoxide was performed using various types of palladium catalysts together with many types of N-donor ligands. The effect of reaction time, pressure, temperature, ligand amount, and molar ratio to establish the optimized conditions was also investigated. With this, we were able to achieve up to 100% conversion and 63.5% yield with PdCl2 and alkylimidazole system (1:3) within 2 h at 220 °C and 1400 psi of CO in toluene.
Development of tyrosinase labile protecting groups for amines
Osborn, Helen M. I.,Williams, Nana Aba O.
, p. 3111 - 3113 (2004)
(Chemical Equation Presented) The development of two novel protecting groups for amines is described. Thus, a range of amines have been converted to ureas, and the deprotection of these upon exposure to mushroom tyrosinase (E.C. 1.14.18.1) has been demonstrated.
Reactivity of Carbamoyl Radicals: the First General and Convenient Free-radical Synthesis of Isocyanates
Minisci, Francesco,Coppa, Fausta,Fontana, Francesca
, p. 679 - 680 (1994)
The first free-radical synthesis of isocyanates was performed by oxidation of oxalic acid monoamides by S2O82-, catalysed by silver(I) and copper(II) salts, in a two-phase system.