64544-71-4Relevant 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.
Synthesis of unsymmetrical phenylurea derivatives via oxidative cross coupling of aryl formamides with amines under metal-free conditions
Reddy, Nagireddy Veera,Kumar, Pailla Santhosh,Reddy, Peddi Sudhir,Kantam, Mannepalli Lakshmi,Reddy, Kallu Rajender
, p. 805 - 809 (2015/02/19)
A new synthetic approach for phenylurea derivatives involving the cross coupling of N-aryl formamides with amines through the formation of isocyanate intermediates in the presence of hypervalent iodine reagents is described.
Radical fixation of functionalized carbon resources: α-sp 3C - H carbamoylation of tertiary amines with aryl isocyanates
Yoshimitsu, Takehiko,Matsuda, Kenichi,Nagaoka, Hiroto,Tsukamoto, Koji,Tanaka, Tetsuaki
, p. 5115 - 5118 (2008/03/28)
A new carbamoylation of tertiary amines is reported. This rare C - H transformation features the direct generation of α-aminoalkyl radicals from tertiary amines, followed by the addition of the resultant nucleophilic radicals to isocyanates, enabling unique access to N,N-dialkylated amino acid derivatives. The authors put forward a mechanistic proposal that is based on the isolation of borinamides produced by capturing nitrogen radical intermediates with Et3B. The present transformation provides a novel one-step process for producing mepivacaine, a clinically important local anesthetic, from readily available materials.
Molecular Scaffolds I: Intramolecular Hydrogen Bonding in a Family of Di- and Triureas
Nowick, James S.,Powell, Noel A.,Martinez, Eduardo J.,Smith, Eric M.,Noronha, Glenn
, p. 3763 - 3765 (2007/10/02)
Di- and triurea derivatives 1 can be prepared by an iterative procedure and are found to exist in intramolecularly hydrogen bonded 10-membered ring conformations, in which substituents R1 and R2 and hydrogen bonding control the direction of the urea carbonyl groups.
NOVEL DESULFURIZATION OF THIOCARBONYL COMPOUNDS INTO THEIR CORRESPONDING OXO-DERIVATIVES USING A PEROXY-SULFUR INTERMEDIATE GENERATED FROM 2-NITROBENZENESULFONYL CHLORIDE AND SUPEROXIDE ANION.
Kim, Yong Hae,Chung, Bong Chul,Chang, Hae Sung
, p. 1079 - 1082 (2007/10/02)
Thiocarbonyl compounds such as substituted-thioureas, -thioamides, and -thiocarbamates were found to react with a peroxysulfur intermediate (3) which is generated by the treatment of 2-nitrobenzenesulfonyl chloride with potassium superoxide to convert into the corresponding carbonyl compounds in quantitative yield at -30 oC in acetonitrile.
FACILE CONVERSION OF 1,3-DISUBSTITUTED THIOUREAS TO THE CORRESPONDING UREAS BY SUPEROXIDE RADICAL ANION (O2.-) IN DIMETHYL SULFOXIDE
KIM, Yong Hae,YON, Gyu Hwan,KIM, Hyung Jin
, p. 309 - 312 (2007/10/02)
Treatment of 1,3-disubstituted thioureas with superoxide radical anion (O2.-) at 20 deg C in dimethyl sulfoxide resulted in the formation of 1,3-disubstituted ureas in excellent yields.The desulfurization appears to proceed by the formation of peroxy-sulfur intermediates such as peroxy-sulfenate, -sulfinate and/or -sulfonate.
