766-93-8Relevant articles and documents
Non-hydrolytic chemoselective cleavage of Ugi tertiary amides: A mild access to N-substituted α-amino acid amides
Giustiniano, Mariateresa,Pelliccia, Sveva,Novellino, Ettore,Tron, Gian Cesare
, p. 1196 - 1199 (2018)
N-Substituted α-amino acid amides can be easily obtained in two steps using the four-component Ugi reaction followed by chemoselective cleavage of the resulting tertiary amide. The use of the sacrificial acid, 2-hydroxymethylbenzoic acid is associated to
Kinetics and mechanism of acid-catalyzed hydrolysis of cyclohexyl isocyanide and pKa determination of N-cyclohexylnitrilium ion
Sung, Kuangsen,Chen, Chao-Chih
, p. 4845 - 4848 (2001)
A novel mechanism for acid-catalyzed hydrolysis of cyclohexyl isocyanide is proposed. It is specific acid/general base catalysis, involving a fast, pre-equilibrium C-protonation of the isocyanide, followed by a rate-determining attack of water on the electron-deficient carbon of the protonated isocyanide. The pKa of N-cyclohexylnitrilium ion was determined to be 0.86±0.05.
Facile N-Formylation of Amines on Magnetic Fe3O4?CuO Nanocomposites
Datta Khanal, Hari,Mishra, Kanchan,Rok Lee, Yong
, p. 4477 - 4484 (2021/08/30)
A facile, eco-friendly, efficient, and recyclable heterogeneous catalyst is synthesized by immobilizing copper impregnated on mesoporous magnetic nanoparticles. The surface chemistry analysis of Fe3O4?CuO nanocomposites (NCs) by XRD and XPS demonstrates the synergistic effect between Fe3O4 and CuO nanoparticles, providing mass-transfer channels for the catalytic reaction. TEM images clearly indicate the impregnation of CuO onto mesoporous Fe3O4. This hydrothermally synthesized eco-friendly and highly efficient Fe3O4?CuO NCs are applied as a magnetically retrievable heterogeneous catalyst for the N-formylation of wide range of aliphatic, aromatic, polyaromatic and heteroaromatic amines using formic acid as a formylating agent at room temperature. The catalytic activity of the NCs for N-formylation is attributable to the synergistic effect between Fe3O4 and CuO nanoparticles. The N-formylated product is further employed for the synthesis of biologically active quinolone moieties.
Chromium-catalysed efficient: N -formylation of amines with a recyclable polyoxometalate-supported green catalyst
Dan, Demin,Chen, Fubo,Zhao, Whenshu,Yu, Han,Han, Sheng,Wei, Yongge
supporting information, p. 90 - 94 (2021/01/11)
A simple and efficient protocol for the formylation of amines with formic acid, catalyzed by a polyoxometalate-based chromium catalyst, is described. Notably, this method shows excellent activity and chemoselectivity for the formylation of primary amines; diamines have also been successfully employed. Importantly, the chromium catalyst is potentially non-toxic, environmentally benign and safer than the widely used high valence chromium catalysts such as CrO3 and K2Cr2O7. The catalyst can be recycled several times with a negligible impact on activity. Finally, a plausible mechanism is provided based on the observation of intermediate and control experiments.
Catalyst freeN-formylation of aromatic and aliphatic amines exploiting reductive formylation of CO2using NaBH4
Kumar, Arun,Kumar, Yashwant,Mahajan, Dinesh,Sharma, Nidhi,Sharma, Pankaj
, p. 25777 - 25787 (2021/08/05)
Herein, we report a sustainable approach forN-formylation of aromatic as well as aliphatic amines using sodium borohydride and carbon dioxide gas. The developed approach is catalyst free, and does not need pressure or a specialized reaction assembly. The reductive formylation of CO2with sodium borohydride generates formoxy borohydride speciesin situ, as confirmed by1H and11B NMR spectroscopy. Thein situformation of formoxy borohydride species is prominent in formamide based solvents and is critical for the success of theN-formylation reactions. The formoxy borohydride is also found to promote transamidation reactions as a competitive pathway along with reductive functionalization of CO2with amine leading toN-formylation of amines.