34065-04-8Relevant academic research and scientific papers
Electrochemical strategies for: N -cyanation of secondary amines and α C -cyanation of tertiary amines under transition metal-free conditions
Cai, Hu,Fu, Yaping,Fu, Zhengjiang,Guo, Shengmei,Hao, Guangguo,Yi, Xuezheng,Yin, Jian,Zhong, Tingting
supporting information, p. 9422 - 9427 (2021/12/09)
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
Synthesis of Cyanamides via a One-Pot Oxidation-Cyanation of Primary and Secondary Amines
Kuhl, Nadine,Raval, Saurin,Cohen, Ryan D.
supporting information, p. 1268 - 1272 (2019/03/07)
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.
Unusual mechanism of the methanolysis of 1-cyanoformamidines
Florea, Cristina,Hǐrtopeanu, Anca,Stavarache, Cristina,Petride, Horia
, p. 191 - 197 (2019/07/31)
Base-catalyzed methanolysis of N-benzyl-N-methyl-1- cyanoformamidine (7) gives methyl N-benzyl-N-methylcarbamimidate (8) as final reaction product. Transient formation of N-benzyl-N-methylcyanamide (9) was observed also. Kinetic data showed two competitive routes in action: (i) 7 → 9 → 8 and (ii) directly 7 → 8. The proposed reaction mechanism is based on the dual behaviour of 7: (i) as an acid and (ii) as an electrophile.
Ruthenium-Catalyzed [2 + 2 + 2] Cycloaddition Reaction Forming 2-Aminopyridine Derivatives from α,ω-Diynes and Cyanamides
Ye, Fei,Haddad, Mansour,Ratovelomanana-Vidal, Virginie,Michelet, Véronique
supporting information, p. 1104 - 1107 (2017/03/14)
A novel, efficient, and mild synthetic route for the preparation of 2-aminopyridines via ruthenium-mediated [2 + 2 + 2] cycloaddition of α,ω-diynes and cyanamides has been developed. This atom-economical catalytic process demonstrated remarkable regioselectivities to access pyridine derivatives of high synthetic utility.
A allyl uncle amine compound by one-step synthesis method of cyano uncle amine compound (by machine translation)
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Paragraph 0079-0087, (2017/09/01)
The invention relates to a one-step synthesis of amine compound allyl unclecyano uncle amine compounds, which belongs to the technical field of organic synthetic method. The method specific synthetic process is as follows: in the airtight reaction environment, to the anhydrous organic solvent is added in the cyanogen bromide, under protection of inert gas, and then added dropwise to the solution in the allylic and high yield amine compound, to obtain allyl uncle amine compound concentration is 0.8 - 1 mol/L solution, at room temperature the reaction 16 - 24 hours later, after column chromatography separation and purification, to obtain a corresponding cyano uncle amine compound. The method to get rid of the expensive deallylation use of the catalyst, the synthesis step is less, raw materials are easy, cheap, mild reaction conditions, the operation is simple, easy to craft and industrialization. Yield 50% - 80% between. (by machine translation)
Synthesis of Cyanamides from Cyanogen Bromide under Mild Conditions through N-Cyanation of Allylic Tertiary Amines
Liang, Honggang,Bao, Lingxiang,Du, Yao,Zhang, Yiying,Pang, Siping,Sun, Chenghui
supporting information, p. 2675 - 2679 (2017/10/06)
Cyanamides were selectively formed through a one-step nucleophilic substitution reaction of allylic tertiary amines with cyanogen bromide. Because of the mild reaction conditions and good yields of the reaction, as well as the commercial availability of the starting materials, this new method represents a valuable tool for the synthesis of cyan-amides through an N-deallylation reaction and an N-cyanation reaction in one pot.
Hepatitis C virus inhibitors
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Page/Page column 387, (2017/01/23)
Hepatitis C virus inhibitors having the general formula (I) are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
N-Cyanation of Secondary Amines Using Trichloroacetonitrile
Ayres, James N.,Ling, Kenneth B.,Morrill, Louis C.
supporting information, p. 5528 - 5531 (2016/11/17)
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.
1-Cyanoformamidines. Formation during the RuO4-mediated oxidation of secondary amines
Florea, Cristina,Stavarache, Cristina,Petride, Horia
, p. 319 - 325 (2016/10/11)
When performed in the presence of cyanide and at pH smaller than 5, the RuO4-mediated oxidation of secondary amines Bn-NH-R (1a-b; R=Me, Et) gave mainly 1-cyanoformamidines Bn-NR-C(=NH)-CN (2a-b) and their hydrolysis products Bn-NR-COCN (3a-b), Bn-NR-CN (4a-b), Bn-NR-CONH2 (5a-b). Carboxamides 5a-b can result also directly from 1a-b. (Chemical Equation Presented).
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
Klein, Pieter J.,Christiaans, Johannes A.M.,Metaxas, Athanasios,Schuit, Robert C.,Lammertsma, Adriaan A.,Van Berckel, Bart N.M.,Windhorst, Albert D.
, p. 1189 - 1206 (2015/03/04)
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.
