824-48-6Relevant articles and documents
Copper-Catalyzed Cascade N-Dealkylation/N-Methyl Oxidation of Aromatic Amines by Using TEMPO and Oxygen as Oxidants
Li, Dianjun,Wang, Shihaozhi,Yang, Jiale,Yang, Jinhui
supporting information, p. 6768 - 6772 (2021/12/31)
A novel tandem N-dealkylation and N-methyl aerobic oxidation of tertiary aromatic amines to N-arylformamides using copper and TEMPO has been developed. This methodology suggested an alternative synthetic route from N-methylarylamines to N-arylformamides.
Citric acid stabilized on the surface of magnetic nanoparticles as an efficient and recyclable catalyst for transamidation of carboxamides, phthalimide, urea and thiourea with amines under neat conditions
Arefi, Marzban,Kazemi Miraki, Maryam,Mostafalu, Ramin,Satari, Mohammad,Heydari, Akbar
, p. 393 - 400 (2019/01/28)
Abstract: Citric acid-coated magnetic nanoparticles (Fe3O4–CA NPs) were successfully prepared and characterized. This magnetic nanocatalyst was employed as an efficient, recyclable, and environmentally benign heterogeneous catalyst for the transamidation of carboxamides, phthalimide, urea and thiourea with amines. Several derivatives of formylated and transamidated products were synthesized in good to excellent yields in the presence of this catalytic system. And, the catalyst could be easily separated from the reaction mixture using an external magnet and can be reused six times without any significant loss in its catalytic activity. Graphical abstract: [Figure not available: see fulltext.].
Consecutive Lossen rearrangement/transamidation reaction of hydroxamic acids under catalyst- and additive-free conditions
Jia, Mengmeng,Zhang, Heng,Lin, Yongjia,Chen, Dimei,Chen, Yanmei,Xia, Yuanzhi
, p. 3615 - 3624 (2018/05/26)
The Lossen rearrangement is a classic process for transforming activated hydroxamic acids into isocyanate under basic or thermal conditions. In the current report we disclosed a consecutive Lossen rearrangement/transamidation reaction in which unactivated hydroxamic acids were converted into N-substituted formamides in a one-pot manner under catalyst- and additive-free conditions. One feature of this novel transformation is that the formamide plays triple roles in the reaction by acting as a readily available solvent, a promoter for additive-free Lossen rearrangement, and a source of the formyl group in the final products. Acyl groups other than formyl could also be introduced into the product when changing the solvent to other low molecular weight aliphatic amide derivatives. The solvent-promoted Lossen rearrangement was better understood by DFT calculations, and the intermediacy of isocyanate and amine was supported well by experiments, in which the desired products were obtained in excellent yields under similar conditions. Not only monosubstituted formamides were synthesized from hydroxamic acids, but also N,N-disubstituted formamides were obtained when secondary amines were used as precursors.
