- Synthesis method of cyanamide
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The invention relates to the field of synthesis of chemical products, in particular to a synthesis method of a cyanamide compound. According to the method, cyanamide is efficiently synthesized under the conditions of air and room temperature by starting from easily available secondary amine compounds, taking cheap and green TMSCN as a cyanide source and adopting green and pollution-free current as a reaction driving agent. Compared with a conventional cyanamide synthesis method, the method disclosed by the invention has the obvious advantages of cheap and easily available reaction raw materials, minimum environmental pollution caused by current, good tolerance to various functional groups on aromatic rings and alicyclic rings, high yield and the like. The method disclosed by the invention can be widely applied to synthesis in the fields of medicines, materials, natural products and the like in industrial and academic circles.
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Paragraph 0041-0042
(2021/08/06)
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- Electrochemical strategies for: N -cyanation of secondary amines and α C -cyanation of tertiary amines under transition metal-free conditions
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Transition metal-free electrochemical approaches for the N-cyanation of secondary amines and the α C-cyanation of tertiary amines have been well established, with products being obtained in moderate to good yields and with good functional group tolerance under ambient conditions. The synthetic application of the protocols has been highlighted through scale-up experiments in a galvanostatic mode. Preliminary mechanistic investigation has confirmed that TBAB played a critical role in N-cyanation transformation and has indicated that the transformation might proceed via a free radical process. This journal is
- Cai, Hu,Fu, Yaping,Fu, Zhengjiang,Guo, Shengmei,Hao, Guangguo,Yi, Xuezheng,Yin, Jian,Zhong, Tingting
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supporting information
p. 9422 - 9427
(2021/12/09)
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- Synthesis of Cyanamides via a One-Pot Oxidation-Cyanation of Primary and Secondary Amines
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An operationally simple oxidation-cyanation method for the synthesis of cyanamides is described. The procedure utilizes inexpensive and commercially available N-chlorosuccinimide and Zn(CN)2 as reagents to avoid direct handling of toxic cyanogen halides. It is demonstrated to be amenable for the cyanation of a variety of primary and secondary amines and aniline derivatives as well as a complex synthetic intermediate en route to verubecestat (MK-8931). Additionally, kinetic measurements and other control experiments are reported to shed light onto the mechanism of this cyanation reaction.
- Kuhl, Nadine,Raval, Saurin,Cohen, Ryan D.
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supporting information
p. 1268 - 1272
(2019/03/07)
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- Synthesis and single crystal structures of substituted-1,3-selenazol-2-amines
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The synthesis and X-ray single crystal structures of a series of new 4-substituted-1,3- selenazol-2-amines is reported. The efficient preparation of these compounds was carried out by two-component cyclization of the selenoureas with equimolar amounts of α-haloketones. The selenoureas were obtained from the reaction of Woollins' reagent with cyanamides, followed by hydrolysis with water. All new compounds have been characterized by IR spectroscopy, multi-NMR (1H, 13C, 77Se) spectroscopy, accurate mass measurement and single crystal X-ray structure analysis.
- Hua, Guoxiong,Du, Junyi,Slawin, Alexandra M.Z.,Woollins, J. Derek
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- N-Cyanation of Secondary Amines Using Trichloroacetonitrile
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A one-pot N-cyanation of secondary amines has been developed using trichloroacetonitrile as an inexpensive cyano source. A diverse range of cyclic and acyclic secondary amines can be readily transformed into the corresponding cyanamides in good isolated yields, with the method successfully utilized in the final synthetic step of a biologically active rolipram-derived cyanamide. This approach exhibits distinct selectivity when compared to the use of highly toxic cyanogen bromide.
- Ayres, James N.,Ling, Kenneth B.,Morrill, Louis C.
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p. 5528 - 5531
(2016/11/17)
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- Synthesis, structure activity relationship, radiolabeling and preclinical evaluation of high affinity ligands for the ion channel of the N-methyl-d-aspartate receptor as potential imaging probes for positron emission tomography
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The N-methyl-d-aspartate receptor (NMDAr) is involved in many neurological and psychiatric disorders including Alzheimer's disease and schizophrenia. Currently, it is not possible to assess NMDAr availability in vivo. The purpose of this study was to develop a positron emission tomography (PET) ligand for the NMDAr ion channel. A series of di- and tri-N-substituted diarylguanidines was synthesized. In addition, in vitro binding affinity for the NMDAr ion channel in rat forebrain membrane fractions was assessed. Compounds 10, 11 and 32 were radiolabeled with either carbon-11 or fluorine-18. Ligands [11C]10 and [18F]32 were evaluated ex vivo in B6C3 mice. Biodistribution studies showed higher uptake of [11C]10 and [18F]32 in forebrain regions compared with cerebellum. In addition, for [11C]10 54% and for [18F]32 70% of activity in the brain at 60 min was due to intact tracer. Pre-treatment with MK-801 (0.6 mg·kg-1, ip) slightly decreased uptake in NMDAr-specific regions for [18F]32, but not for [11C]10. As such [18F]32 has the best characteristics as a PET tracer for the ion channel of the NMDAr.
- Klein, Pieter J.,Christiaans, Johannes A.M.,Metaxas, Athanasios,Schuit, Robert C.,Lammertsma, Adriaan A.,Van Berckel, Bart N.M.,Windhorst, Albert D.
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p. 1189 - 1206
(2015/03/04)
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- A copper-mediated oxidative N-cyanation reaction
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Copper-promoted N-cyanation of aliphatic sec-amine by CuCN is achieved via oxidative coupling. This procedure employs O2 as a clean oxidant. Notably, sulfoximines and 1,1,3,3-tetramethylguanidine also worked well in this procedure. Thus, it represents a key progress in the C-N bond formation reaction as well as in the cyanation reaction. This journal is the Partner Organisations 2014.
- Teng, Fan,Yu, Jin-Tao,Jiang, Yan,Yang, Haitao,Cheng, Jiang
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supporting information
p. 8412 - 8415
(2014/07/22)
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