18773-77-8Relevant academic research and scientific papers
DIBENZOTHIOPHENE SALT AS ALKYNYLATING AND CYANATING AGENT
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Paragraph 0098, (2021/08/27)
The present invention describes a new alkynylation and cyanation agent, as well as its preparation and use to introduce nitrile (cyano) or alkyne groups into chemical target molecules by means of an electrophilic reaction. To enable an electrophilic reaction, the chemical backbone of dibenzothiophene was used.
Synthesis of nitriles via the iodine-mediated dehydrosulfurization of thioamides
Murata, Yuki,Iwasa, Hitomi,Matsumura, Mio,Yasuike, Shuji
, p. 679 - 681 (2020/07/30)
A simple general method for the synthesis of nitriles using the inexpensive and easy to handle iodine (I2) is described herein. The reaction of thioamides with I2 in the presence of triethylamine at room temperature under aerobic conditions afforded various nitriles bearing aryl, vinyl, and alkyl groups in good-to-excellent yields. This method was also effective for conversion from thioureas to cyanamides.
5-(Cyano)dibenzothiophenium Triflate: A Sulfur-Based Reagent for Electrophilic Cyanation and Cyanocyclizations
Li, Xiangdong,Golz, Christopher,Alcarazo, Manuel
supporting information, p. 9496 - 9500 (2019/06/27)
The synthesis of 5-(cyano)dibenzothiophenium triflate 9, prepared by activation of dibenzo[b,d]thiophene-5-oxide with Tf2O and subsequent reaction with TMSCN is reported, and its reactivity as electrophilic cyanation reagent evaluated. The scalable preparation, easy handling and broad substrate scope of the electrophilic cyanation promoted by 9, which includes amines, thiols, silyl enol ethers, alkenes, electron rich (hetero)arenes and polyaromatic hydrocarbons, illustrate the synthetic potential of this reagent. Importantly, Lewis acid activation of the reagent is not required for the transfer process. We additionally report herein biomimetic cyanocyclization cascade reactions, which are not promoted by typical electrophilic cyanation reagents, demonstrating the superior ability of 9 to trigger challenging transformations.
Tris(3,5-dimethylpyrazolyl)methane copper(I) complexes featuring one disubstituted cyanamide ligand
Melekhova, Anna A.,Novikov, Alexander S.,Dubovtsev, Alexey Yu.,Zolotarev, Andrey A.,Bokach, Nadezhda A.
, p. 69 - 74 (2018/09/22)
The complexes [Cu{HC(3,5-Me2pz)3}(NCNR2)][BF4] (1–8; R2 = Me2 1, Et2 2, C5H10 3, C4H8O 4, C4H8 5, C3H
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.
Copper-catalyzed one-pot synthesis of unsymmetrical arylurea derivatives via tandem reaction of diaryliodonium salts with N -arylcyanamide
Li, Pengfei,Cheng, Guolin,Zhang, Hong,Xu, Xianxiang,Gao, Jingyuan,Cui, Xiuling
, p. 8156 - 8162 (2015/03/18)
An efficient "one-pot" approach to multiple substituted ureas from N-arylcyanamide and diaryliodonium salts has been presented. The two-step procedure involved the weak base-promoted chemoselective arylation of secondary amines with diaryliodonium and Cu-catalyzed nucleophilic addition of N-arylcyanamide with second diaryliodonium. The diverse unsymmetrical arylureas were obtained in up to 91% yield for 29 examples.
Nickel-catalyzed [2+2+2] cycloaddition of diynes and cyanamides
Stolley, Ryan M.,MacZka, Michael T.,Louie, Janis
experimental part, p. 3815 - 3824 (2011/09/16)
A variety of bicyclic N,N-disubstituted 2-aminopyridines have been prepared from diynes and cyanamides by nickel-catalyzed [2+2+2] cycloaddition reactions. The reactions proceeded at room temperature with low catalyst loading to afford 2-aminopyridines in
HETEROCYCLIC DERIVATIVE HAVING INHIBITORY ACTIVITY ON TYPE-I 11 -HYDROXYSTEROID DEHYDROGENASE
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Page/Page column 34, (2010/08/07)
Disclosed is a compound which is useful as an 11β-hydroxysteroid dehydrogenase type 1 inhibitor. A compound represented by the formula: its pharmaceutically acceptable salt, or a solvate thereof, wherein X is O or S, a broken line and a wavy line represent the presence or the absence of a bond, (i) when a broken line represents the presence of a bond, a wavy line represents the absence of a bond, R2 and R3 are each independently hydrogen, halogen, cyano, hydroxy, carboxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like, (ii) when a broken line represents the absence of a bond, a wavy line represents the presence of a bond, R1 and R4 are each independently hydrogen, halogen or the like, R2 and R3 are each independently hydrogen, halogen, cyano, hydroxy, carboxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like, and R5 and R6 are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like.
1-Cyanoimidazole as a mild and efficient electrophilic cyanating agent
Wu, Yong-Qian,Limburg, David C.,Wilkinson, Douglas E.,Hamilton, Gregory S.
, p. 795 - 797 (2007/10/03)
formula presented A mild and high-yielding cyanating reaction of amine, sulfur, and carbanion nucleophiles is reported here using 1-cyanoimidazole as an electrophilic cyanating agent.
