104810-17-5Relevant articles and documents
Electroreductive synthesis of polyfunctionalized pyridin-2-ones from acetoacetanilides and carbon disulfide with oxygen evolution
Gao, Shulin,Hu, Xi,Li, Weili,Li, Yanni,Liang, Deqiang,Ma, Zhongxiao,Wang, Baoling,Xu, Lichun,Zhang, Xin
supporting information, p. 1013 - 1018 (2022/02/16)
A chemical reductant or a sacrificial electron donor is required in any reduction reactions, generally resulting in undesired chemical waste. Herein, we report a reductant-free reductive [3 + 2 + 1] annulation of β-keto amides with CS2 enabled by the synergy of electro/copper/base using water as an innocuous anodic sacrifice with O2 as a sustainable by-product. This electrochemical protocol is mild and provides access to polyfunctionalized pyridin-2-ones from simple starting materials in a single step.
Selective Reduction of Nitroarenes to Arylamines by the Cooperative Action of Methylhydrazine and a Tris(N-heterocyclic thioamidate) Cobalt(III) Complex
Ioannou, Dimitris I.,Gioftsidou, Dimitra K.,Tsina, Vasiliki E.,Kallitsakis, Michael G.,Hatzidimitriou, Antonios G.,Terzidis, Michael A.,Angaridis, Panagiotis A.,Lykakis, Ioannis N.
, p. 2895 - 2906 (2021/02/27)
We report an efficient catalytic protocol that chemoselectively reduces nitroarenes to arylamines, by using methylhydrazine as a reducing agent in combination with the easily synthesized and robust catalyst tris(N-heterocyclic thioamidate) Co(III) complex [Co(κS,N-tfmp2S)3], tfmp2S = 4-(trifluoromethyl)-pyrimidine-2-thiolate. A series of arylamines and heterocyclic amines were formed in excellent yields and chemoselectivity. High conversion yields of nitroarenes into the corresponding amines were observed by using polar protic solvents, such as MeOH and iPrOH. Among several hydrogen donors that were examined, methylhydrazine demonstrated the best performance. Preliminary mechanistic investigations, supported by UV-vis and NMR spectroscopy, cyclic voltammetry, and high-resolution mass spectrometry, suggest a cooperative action of methylhydrazine and [Co(κS,N-tfmp2S)3] via a coordination activation pathway that leads to the formation of a reduced cobalt species, responsible for the catalytic transformation. In general, the corresponding N-arylhydroxylamines were identified as the sole intermediates. Nevertheless, the corresponding nitrosoarenes can also be formed as intermediates, which, however, are rapidly transformed into the desired arylamines in the presence of methylhydrazine through a noncatalytic path. On the basis of the observed high chemoselectivity and yields, and the fast and clean reaction processes, the present catalytic system [Co(κS,N-tfmp2S)3]/MeNHNH2 shows promise for the efficient synthesis of aromatic amines that could find various industrial applications.
[1+1] Copper(II) macrocyclic Schiff base complex on rGO as a photocatalyst for reduction of nitroaromatics compounds under visible-light irradiation
Ghalebin, Saeed Nasiri,Bezaatpour, Abolfazl,Sadr, Moayad Hossaini,Sadjadi, Mirabdullah Seyed,Moghaddam, Mohammad Khodadadi,Szunerits, Sabine
, (2021/01/26)
In this work, [1 + 1] macrocyclic Copper(II) Schiff base complex ([CuL](NO3)2.H2O) was synthesized and grafted on reduced graphene oxide successfully. The novel prepared sample was characterized by physico-chemical techniques and used as a photocatalyst for the reduction of nitroaromatic compounds to their amine derivatives at room temperature under visible-light irradiation with hydrazine mono hydrate. From the prepared samples, reduced graphene oxide loaded with 30% [CuL](NO3)2.H2O catalyst (rGO/CuM30) shows the best efficiency for converting different nitroaromatic compounds to the corresponding amino compounds using visible light. As-prepared catalyst illustrated excellent activity for the reduction of 2-nitrophenol to 2-aminophenol (100% conversion) in only 90 min. Finally, the catalyst could be recovered for five times and reused without decreasing of its efficiency.
