53693-58-6Relevant academic research and scientific papers
2,2,2-Trifluroenthanol promoted synthesis of unsymmetrical ureas from dioxazolones and amines via tandem lossen rearrangement/condensation process
Li, Jian,He, Wang,Lei, Pan,Song, Jiacheng,Huo, Jiyou,Wei, Hongbo,Bai, Hongjin,Xie, Weiqing
supporting information, p. 3590 - 3600 (2021/10/07)
A 2,2,2-trifluroenthanol (TFE) promoted synthesis of unsymmetric ureas was described. This approach enabled the construction of a variety of ureas from the readily prepared and easy-to-handle dioxazolones and amines via tandem Lossen rearrangement/condensation process. The reaction featured mild conditions for the urea synthesis under metal-free conditions, which was successively applied in the scale-up synthesis of herbicides Monuro and Isoproturon.
A Novel C–N Migration Rearrangement Based on N–F Compounds for the Synthesis of N-Alkyl Diaryl Ureas
Zhao, Yi-Xiao,Xie, Tian,Yang, San-Ke,Yang, Xian-Jin
, p. 437 - 445 (2020/01/22)
A novel rearrangement reaction based on the structure of N-fluoro-N-(phenylsulfonyl) benzamides (FPSBA) was developed. In the presence of base, unsymmetrical N-alkyl diaryl ureas were obtained in good yields which were accomplished through secondary alkyl phenylamines initiated 1,2-phenyl-shift migration rearrangement of N-fluoro-N-(phenylsulfonyl) benzamides. The reaction was carried out without using traditional, highly toxic reagents and noble metals. Whereas without rearrangement occurrence for primary phenylamines and aliphatic amines, normal amides and N-(phenylsulfonyl) benzamides were afforded respectively. Nitrene and phenyl isocyanate included process were prevented and a secondary alkyl phenylamine initiated vicinal SN2' reaction occurred. This rearrangement reaction features an interesting reaction mechanism, mild reaction conditions, simple operation, and useful products.
Pd(II)/Ag(I)-Promoted One-Pot Synthesis of Cyclic Ureas from (Hetero)Aromatic Amines and Isocyanates
Youn, So Won,Kim, Yi Hyun
supporting information, p. 6140 - 6143 (2016/12/09)
A simple and facile one-pot reaction has been developed to afford a diverse range of N,N′-disubstituted benzimidazolones and imidazopyridinones containing two differently substituted N atoms. A cooperative Pd(II)/Ag(I) system promotes the sequential addition/intramolecular C-H amidation reaction of (hetero)aromatic amines and isocyanates, leading to the formation of two C-N bonds. A mechanism involving radical intermediates generated by single-electron transfer (SET) in the presence of a Ag2CO3 oxidant and Pd(OAc)2 Lewis acid is proposed. This protocol offers an operationally easy, simple, and robust approach with the use of readily available starting materials, good functional group tolerance, and high efficiency.
Insertion of isocyanates, CO2, and ethylene carbonate into the Zr-C and Zr-N bonds of imine complexes. Construction of chiral centers like those in α-amino acids
Gately, Daniel A.,Norton, Jack R.,Goodson, Patricia A.
, p. 986 - 995 (2007/10/02)
In some cases zirconocene-imine complexes insert CO2; more generally they insert isocyanates and cyclic carbonates. Isocyanates can insert into either the Zr-C or the Zr-N bond; protonolysis of the zirconacycle resulting from Zr-C insertion giv
DIAZANICKELACYCLOPENTANONE AUS NICKEL(0), IMINEN UND ISOCYANATEN
Hoberg, Heinz,Suemmermann, Klaus
, p. 383 - 390 (2007/10/02)
Isocyanates are oxidatively coupled with imines at nickel(0) under the influence of basic chelate ligands to form diazanickelacyclopentanones.The structure of these novel five-membered nickelacycles has been determined by spectroscopic and chemical methods.The mechanism of the coupling reaction is discussed.
