5663-04-7Relevant articles and documents
Construction of Benzimidazolone Derivatives via Aryl Iodide Catalyzed Intramolecular Oxidative C-H Amination
Wang, Yang,Sun, Yuan-Yuan,Cui, Yi-Mo,Yu, Ying-Xin,Wu, Zheng-Guang
, p. 3234 - 3241 (2022/03/23)
The first aryl iodide catalyzed intramolecular C-H amination of phenylurea has been disclosed for high-efficiency synthesis of benzimidazolone derivatives in excellent yields (up to 97%) by an operationally simple one-step organocatalytic oxidative proces
Iron(II)-Catalyzed Hydroamination of Isocyanates
South, Amy J.,Geer, Ana M.,Taylor, Laurence J.,Sharpe, Helen R.,Lewis, William,Blake, Alexander J.,Kays, Deborah L.
supporting information, p. 4115 - 4120 (2019/10/17)
A two-coordinate Fe(II) m-terphenyl complex acts as a precatalyst for the hydroamination of isocyanates, affording urea and biuret derivatives, with product selectivity accomplished via modification of the reaction conditions. Using a more nucleophilic amine facilitates the insertion of up to four isocyanates into the N-H bond, affording triuret and tetrauret derivatives.
Structural Aspects of Thermally Cleavable Adducts Derived from the Reaction of Imidazolines with Isocyanates
Laue, Andreas,Preu?, Andrea,Heck, Manuel,Martin, Mandy,Binner, Marcus,Rüffer, Tobias,Anders, Susann,Werner, Carsten,Kroll, Lothar,Lang, Heinrich,Spange, Stefan
, p. 4431 - 4442 (2016/12/14)
The reaction of isocyanates with substituted imidazolines and the thermally induced cleavage of the resulting adducts are presented. For this purpose, reactions of various isocyanates [ethyl isocyanate, p-methylphenyl isocyanate, phenyl isocyanate, p-(trifluoromethyl)phenyl isocyanate] with 1-alkylimidazoline derivatives have been studied as a function of the substituent at the 2-position of the imidazoline ring. Three equivalents of isocyanate react with one equivalent of 1-ethylimidazoline to give a stoichiometric well-defined adduct. However, 1-ethyl-2-isopropylimidazoline reacts with isocyanates at 0 °C in another way, with formation of 2:1 adducts which belong to the family of 1,3-diphenyltetrahydroimidazo[1,2-a][1,3,5]triazine-2,4(1H,3H)-diones. The reaction of 1-ethyl-2-methylimidazoline with aromatic isocyanates at 0 °C also leads to 2:1 adducts, in this case of a malonamide type, which can react at 60 °C with an additional isocyanate equivalent to give the known pyrimidinediones. Thermal analysis (TG-MS/DSC) and trapping reactions with nucleophilic reagents, such as diphenylamine, show the release of isocyanate during the thermally induced cleavage reaction. Thus, blocked isocyanates are available by the reaction of isocyanates with 1-ethylimidazoline or 1-ethyl-2-isopropylimidazoline.