18522-99-1Relevant articles and documents
Supporting-Electrolyte-Free Anodic Oxidation of Oxamic Acids into Isocyanates: An Expedient Way to Access Ureas, Carbamates, and Thiocarbamates
Petti, Alessia,Fagnan, Corentin,van Melis, Carlo G. W.,Tanbouza, Nour,Garcia, Anthony D.,Mastrodonato, Andrea,Leech, Matthew C.,Goodall, Iain C. A.,Dobbs, Adrian P.,Ollevier, Thierry,Lam, Kevin
supporting information, p. 2614 - 2621 (2021/06/27)
We report a new electrochemical supporting-electrolyte-free method for synthesizing ureas, carbamates, and thiocarbamates via the oxidation of oxamic acids. This simple, practical, and phosgene-free route includes the generation of an isocyanate intermediate in situ via anodic decarboxylation of an oxamic acid in the presence of an organic base, followed by the one-pot addition of suitable nucleophiles to afford the corresponding ureas, carbamates, and thiocarbamates. This procedure is applicable to different amines, alcohols, and thiols. Furthermore, when single-pass continuous electrochemical flow conditions were used and this reaction was run in a carbon graphite Cgr/Cgr flow cell, urea compounds could be obtained in high yields within a residence time of 6 min, unlocking access to substrates that were inaccessible under batch conditions while being easily scalable.
Visible light-mediated photocatalytic oxidative cleavage of activated alkynes: Via hydroamination: A direct approach to oxamates
Arepally, Sagar,Katta, Narenderreddy,Murugan, Arumugavel,Ojha, Mamata,Sharada, Duddu S.
, p. 12599 - 12603 (2020/04/24)
The direct oxidative cleavage of activated alkynes via hydroamination has been described using organic photocatalyst under visible-light irradiation at room temperature. In this reaction, the single electron oxidation of an in situ formed enamine followed by radical coupling with an oxidant finally delivers the oxamate. The key features of this photocatalytic reaction are the mild reaction conditions, metal-free organic dye as a photocatalyst, and TBHP playing a dual role as O source and for the regeneration of the photocatalyst.
The development of tetrazole derivatives as protein arginine methyltransferase I (PRMT I) inhibitors
Sun, Yutong,Wang, Zhe,Yang, Hao,Zhu, Xuanli,Wu, Han,Ma, Lu,Xu, Fang,Hong, Wei,Wang, Hao
, (2019/09/03)
Protein arginine methyltransferase 1 (PRMT1) can catalyze protein arginine methylation by transferring the methyl group from S-adenosyl-L-methionine (SAM) to the guanidyl nitrogen atom of protein arginine, which influences a variety of biological processes. The dysregulation of PRMT1 is involved in a diverse range of diseases, including cancer. Therefore, there is an urgent need to develop novel and potent PRMT1 inhibitors. In the current manuscript, a series of 1-substituted 1H-tetrazole derivatives were designed and synthesized by targeting at the substrate arginine-binding site on PRMT1, and five compounds demonstrated significant inhibitory effects against PRMT1. The most potent PRMT1 inhibitor, compound 9a, displayed non-competitive pattern with respect to either SAM or substrate arginine, and showed the strong selectivity to PRMT1 compared to PRMT5, which belongs to the type II PRMT family. It was observed that the compound 9a inhibited the functions of PRMT1 and relative factors within this pathway, and down-regulated the canonical Wnt/β-catenin signaling pathway. The binding of compound 9a to PRMT1 was carefully analyzed by using molecular dynamic simulations and binding free energy calculations. These studies demonstrate that 9a was a potent PRMT1 inhibitor, which could be used as lead compound for further drug discovery.
Tethered NHC Ligands for Stereoselective Alkyne Semihydrogenations
Pape, Felix,Teichert, Johannes F.
supporting information, p. 2470 - 2482 (2017/05/22)
A copper(I)-catalyzed semihydrogenation of internal alkynes has been developed. A variety of oxygen- and nitrogen-tethered N-heterocyclic carbene (NHC) complexes have been investigated, leading to a highly Z-selective transformation. The catalyst is generated from inexpensive copper(I) chloride in situ and allows catalytic semihydrogenation down to 10 bar H2.
Improved microwave synthesis of unsymmetrical N,N'-diaryl-1,2-aminoethane and imidazolidinium salts as precursors of N-heterocyclic carbenes
Ibrahim, Yehia A.,Al-Awadi, Nouria A.,Al-Azemi, Talal F.,John, Elizabeth
, p. 38869 - 38876 (2014/11/08)
Lithium aluminium hydride reduction of bis-unsymmetric-diaryloxamides 3 is difficult to accomplish especially for the sterically hindered mesityl derivative. Using microwaves LAH reduction of 3a,d was successful in a short time, however, with cleavage of the ether linkage to give compounds 11a,d. Extension of this method enabled the reduction of bis-oxamide derivatives 13 to the corresponding tetraamine derivative 14 which was then converted to the bis-imidazolidinium salt 15. Application of this method led to rapid reduction of unsymmetric N,N'-diaryloxamides 16 to the corresponding N,N'- diarylethylenediamines 17 which were converted to their corresponding imidazolidinium salts 18. the Partner Organisations 2014.
A transformation of N-alkylated anilines to N-aryloxamates
Zhu, Xiao-He,Zhang, Xin,Xin, Hong-Xing,Yan, Hong
, p. 1542 - 1547 (2013/09/02)
Transformation of N-alkylated anilines to N-aryloxamates was studied using ethyl 2-diazoacetoacetate as an alkylating agent and dirhodium tetraacetate (Rh2(OAc)4) as the catalyst. The general applicability of the reaction as a synthetic method for N-aryloxamates was studied with a number of substituted N-alkylated anilines. The results revealed that the oxamate was formed by a radical reaction with molecular O2 and Rh 2(OAc)4 as initiator. Copyright
New Highlights in the Synthesis of 4-Aryl-1,4-dihydropyrazines
He, Jing-Yu,Song, Xiu-Qing,Yan, Hong,Zhong, Ru-Gang
, p. 1357 - 1361 (2013/02/23)
The 4-aryl-1,4-dihydropyrazines were prepared via the cyclization of N,N-bisalkylated anilines with ammonium acetate. These reactions were aided by improvements in the synthesis of N,N-bisalkylated anilines which were alkylated with anilines using ethyl 2-diazo acetoacetate in a reaction catalyzed by rhodium acetate in the absence of oxygen. A possible mechanistic route is postulated on the basis of the isolation of the N-alkylation intermediates, which were determined to be N-aryloxamates by 1H NMR data and X-ray diffraction.
Pd-catalyzed tandem cyclization of ethyl glyoxalate and amines: Rapid assembly of highly substituted cyclic dehydro-α-amino acid derivatives
Luo, Yueting,Lu, Xiaoxia,Ye, Yong,Guo, Ya,Jiang, Huanfeng,Zeng, Wei
supporting information, p. 5640 - 5643 (2013/01/15)
A novel cascade cyclization of ethyl glyoxalate and amines proceeds in the presence of Pd(TFA)2 (5 mol %) to give the cyclic dehydro-α-amino acid derivatives. This method provides a fast and simple access to highly substituted dihydro-pyrrol-2-ones in good yields.
Urea activation of α-nitrodiazoesters: An organocatalytic approach to N-H insertion reactions
So, Sonia S.,Mattson, Anita E.
supporting information; experimental part, p. 8798 - 8801 (2012/07/02)
The combination of a urea catalyst and an α-nitro-α-diazo ester gives rise to a reactive species able to undergo insertion into the N-H bonds of anilines. This new strategy to achieve N-H insertion reactivity is in contrast to typical metal-catalyzed cond
Synthesis, structural and biological studies of some oxamic acids and their CoII, NiIIand CuII metal complexes
Kumar, Devendra,Bhadauria, Anupama,Sharma
experimental part, p. 427 - 430 (2012/03/12)
Six new metal complexes of CoII, NlII and Cu II with N-(4-methoxyphenyl)oxamic acid and N-(4-carboxyphenyl)oxamic acid have been synthesized and characterized by elemental analyses, IR, 1H NMR and electronic spe