10272-02-3Relevant academic research and scientific papers
Design, synthesis and X-ray crystallography of selenides bearing benzenesulfonamide moiety with neuropathic pain modulating effects
Angeli, Andrea,di Cesare Mannelli, Lorenzo,Lucarini, Elena,Peat, Thomas S.,Ghelardini, Carla,Supuran, Claudiu T.
, p. 210 - 219 (2018)
A series of selenides bearing benzensulfonamide were investigated as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). Potent inhibitory action, in the low nanomolar range, was detected against isoforms hCA II and VII, which are known to be involved in neuropathic pain modulation. These selenides showed on the other hand moderate inhibition against the cytosolic isoforms hCA I and transmembrane hCA IX. X-ray crystallographic data of two derivatives bound to hCA II allowed us to rationalize the excellent inhibitory data. In a mice model of neuropathic pain induced by oxaliplatin, some of the strong CA II/VII inhibitors induced a long lasting pain relieving effect.
Triselenium dicyanide from malononitrile and selenium dioxide. One-pot synthesis of selenocyanates
Kachanov, Andrey V.,Slabko, Oleg Yu.,Baranova, Olga V.,Shilova, Evgenia V.,Kaminskii, Vladimir A.
, p. 4461 - 4463 (2004)
Triselenium dicyanide is formed by the interaction of malononitrile and selenium dioxide in dimethylsulfoxide or dimethylformamide. Addition of aromatic amines, indoles and some active methylene compounds to this reaction mixture gives the corresponding s
A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions
Zhang, Xing,Wang, Chenguang,Jiang, Hong,Sun, Linhao
, p. 22042 - 22045 (2018)
A low-cost and efficient thio- and selenocyanation strategy for electron-rich arenes has been developed under constant-current electrolytic conditions in an undivided cell. This strategy is versatile for various (hetero)aromatic compounds such as indole, pyrrole, aniline and anisole under mild conditions without any catalyst or oxidant. Readily available salts NH4SCN and KSeCN are employed respectively as the sole reagent.
Catalyst and additive-free regioselective oxidative C-H thio/selenocyanation of arenes and heteroarenes with elemental sulfur/selenium and TMSCN
Feng, Chengtao,Peng, Ya,Ding, Guangrong,Li, Xiangxiao,Cui, Chang,Yan, Yizhe
, p. 13367 - 13370 (2018)
A regioselective oxidative C-H thio/selenocyanation of arenes and heteroarenes with TMSCN and elemental sulfur/selenium was demonstrated under catalyst-free and additive-free conditions. Dimethyl sulfoxide (DMSO) was employed as the mild oxidant as well as the solvent. The reaction is operationally simple and scalable with a broad substrate scope.
Oxidative umpolung selenocyanation of ketones and arenes: An efficient protocol to the synthesis of selenocyanates
Cui, Jianguo,Wei, Meizhen,Pang, Liping,Xiao, JunAn,Gan, Chunfang,Guo, Jiali,Xie, Chuanfang,Zhu, Qiming,Huang, Yanmin
, (2020)
A practical method for the umpolung selenocyanation of aryl ketones, alkyl ketones, β-ketoesters and electron-rich arenes has been developed, affording various selenocyanates in moderate to excellent yields. This transformation proceeds by an oxidative um
An electrochemical method for deborylative seleno/thiocyanation of arylboronic acids under catalyst- And oxidant-free conditions
He, Dongdong,Yao, Jiaojiao,Ma, Boling,Wei, Jinghao,Hao, Guangguo,Tuo, Xun,Guo, Shengmei,Fu, Zhengjiang,Cai, Hu
supporting information, p. 1559 - 1564 (2020/03/26)
An electrochemical deborylative seleno/thiocyanation of arylboronic acids has been well established to synthesize the corresponding aryl seleno/thiocyanates with good functional group tolerance under ambient conditions. A gram-scale reaction has been performed to highlight the advantages of the protocol. Preliminary mechanistic studies indicate that the oxidation of the seleno/thiocyanate anion occurs prior to that of the arylboronic acid substrate in galvanostatic mode, and that free radicals are involved in the process.
Synthesis method of aryl selenocyanate compounds
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Paragraph 0071-0073; 0086, (2020/02/14)
The invention relates to the field of synthesis of chemical products, in particular to a synthesis method of aryl selenocyanate compounds. The method starts from arylboronic acid which is easy to obtain, KSeCN which is the cheapest is used as a selenocyanate source, environment-friendly pollution-free current is adopted as a reaction driver, and under conditions of air and a room temperature, arylselenocyanates are efficiently synthesized. Compared with a conventional aryl selenocyanate synthesis method, the method has the obvious advantages that reaction raw materials (including the arylboronic acid) are cheap and easy to obtain, the current causes the lowest pollution to the environment, multiple kinds of functional groups of aromatic rings have good tolerance, yields are high, and thelike. The method can be applied to synthesis of a wide variety of fields of medicines, materials, natural products and the like of the industrial circles and the academic circles.
Temperature-Controlled Chalcogenation and Chalcogenocyanation of Imidazopyridines in Water under Transition Metal-Free Conditions
Zhu, Yu-Shen,Xue, Yuting,Liu, Wannian,Zhu, Xinju,Hao, Xin-Qi,Song, Mao-Ping
, p. 9106 - 9116 (2020/08/14)
A sustainable and transition metal-free approach for C3 chalcogenation and chalcogenocyanation of imidazopyridines with KXCN (X = S or Se) has been developed under mild conditions. Importantly, this reaction was performed in the presence of catalytic iodi
A convenient, transition metal-free synthesis of difluoromethyl selenoethers from organic selenocyanates and TMSCF2H
Dong, Tao,Nie, Jing,Zhang, Cheng-Pan
, p. 5642 - 5649 (2018/08/22)
An efficient and transition metal-free method for the synthesis of aryl or alkyl difluoromethyl selenides (RSeCF2H) from the corresponding selenocyanates (RSeCN) and TMSCF2H/t-BuOK is described. The reaction performed in THF at 0 °C for 24 h or at room temperature for 6 h supplied a series of RSeCF2H in good to high yields. The successful preparation of difluoromethylselenolated sulfadimethoxine derivative and the scaled-up synthesis of 1-benzyl-5-((difluoromethyl)selanyl)indoline, as examples, suggested good practicability of this method. Advantages of the reaction include mild reaction conditions, good functional group tolerance, a wide range of substrates, and high efficiency. This protocol offered a number of novel difluoromethyl selenoethers, which would accelerate use of such compounds in the areas of life science.
Trifluoromethylselenolation of Aryldiazonium Salts: A Mild and Convenient Copper-Catalyzed Procedure for the Introduction of the SeCF3 Group
Nikolaienko, Pavlo,Rueping, Magnus
supporting information, p. 2620 - 2623 (2016/02/27)
The straightforward introduction of the trifluoromethylseleno group into aromatic and heteroaromatic compounds is accomplished by the utilization of readily available aryldiazonium tetrafluoroborates, potassium selenocyanate, and Ruppert-Prakash reagent. The reaction tolerates a wide range of aromatic and heteroaromatic diazonium salts and is also amenable to the synthesis of pentafluoroethyl selenoethers. Furthermore, the methodology can be applied directly starting from anilines.
