10229-11-5Relevant articles and documents
Modification of the 4-phenylbutyl side chain of potent 3-benzazepine-based GluN2B receptor antagonists
Wagner, Marina,Schepmann, Dirk,Ametamey, Simon M.,Wünsch, Bernhard
, p. 3559 - 3567 (2019)
Excitotoxicity driven by overactivation of NMDA receptors represents a major mechanism of acute and chronic neurological and neurodegenerative disorders. Negative allosteric modulators interacting with the ifenprodil binding site of the NMDA receptor are able to interrupt this ongoing neurodamaging process. Starting from the potent 3-benzazepine-1,7-diol 4a novel NMDA receptor antagonists were designed by modification of the N-(4-phenylbutyl) side chain. With respect to developing novel fluorinated PET tracers, regioisomeric fluoroethoxy derivatives 11, 12, 14, and 15 were synthesized. Analogs 19 and 20 with various heteroaryl moieties at the end of the N-side chain were prepared by Sonogashira reaction and nucleophilic substitution. The fluoroethyl triazole 37 was obtained by 1,3-dipolar cycloaddition. In several new ligands, the flexibility of the (hetero)arylbutyl side chain was restricted by incorporation of a triple bond. The affinity towards the ifenprodil binding site was tested in an established competition assay using [3H]ifenprodil as radioligand. Introduction of a fluoroethoxy moiety at the terminal phenyl ring, replacement of the terminal phenyl ring by a heteroaryl ring and incorporation of a triple bond into the butyl spacer led to considerable reduction of GluN2B affinity. The phenol 15 (Ki = 193 nM) bearing a p-fluoroethoxy moiety at the terminal phenyl ring represents the most promising GluN2B ligand of this series of compounds. With exception of 15 showing moderate σ2 affinity (Ki = 79 nM), the interaction of synthesized 3-benzazepines towards the PCP binding site of the NMDA receptor, σ1 and σ2 receptors was rather low (Ki > 100 nM).
Synthesis of palladated magnetic nanoparticle (Pd@Fe3O4/AMOCAA) as an efficient and heterogeneous catalyst for promoting Suzuki and Sonogashira cross-coupling reactions
Tamoradi, Taiebeh,Daraie, Mansoureh,Heravi, Majid M.
, (2020)
Palladium supported magnetic nanoparticle (Pd@Fe3O4/AMOCAA) was easily prepared in the presence of Scrophularia striata extract and fully characterized by FT-IR, SEM, VSM, TEM, TGA, XRD and EDAX. It was successfully employed as an easily separable and reusable effective heterogeneous catalyst classical Suzuki and Sonogashira cross-coupling reaction. Sustainability of the methodology was reserved by easy recovery of the catalyst using an external magnet and reusing it for 7 times without appreciable loss of its catalytic activity.
Mechanism of the copper-free palladium-catalyzed sonagashira reactions: Multiple role of amines
Tougerti, Asma,Negri, Serge,Jutand, Anny
, p. 666 - 676 (2007)
Amines used as bases in copper-free, palladium-catalyzed Sonogashira reactions play a multiple role. The oxidative addition of iodobenzene with [Pd()(PPh3)4] is faster when performed in the presence of amines (piperidine>m
Tributylmanganate(II)-mediated cyclization of enynes
Usugi,Shinokubo,Oshima
, p. 1903 - 1904 (2000)
Treatment of enynes with tributylmanganate(II) provided cyclized products containing alkylidene substituents. 1-Tridecen-6-yne or 1-tetradecen-7-yne gave 1-heptylidene-2-methylcyclopentane or 1-heptylidene-2-methylcyclohexane in 67 or 50% yield, respectiv
Gold-catalyzed tandem cycloisomerization-hydroalkoxylation of homopropargylic alcohols
Belting, Volker,Krause, Norbert
, p. 4489 - 4492 (2006)
The tandem cycloisomerization-hydroalkoxylation of various homopropargylic alcohols in the presence of an alcohol and a dual catalyst system, consisting of a gold precatalyst and a Bronsted acid, provides an efficient route to tetrahydrofuranyl ethers und
A functionalized ionic liquid containing phosphine-ligated palladium complex for the Sonogashira reactions under aerobic and CuI-free conditions
Zhang, Jing,Crossed, Dakovi? Marijana,Popovi?, Zora,Wu, Haihong,Liu, Ye
, p. 160 - 163 (2012)
A Pd-complex functionalized ionic liquid (IL), di-(1-butyl-2- diphenylphosphino-3-methylimidazolium)-dichloropalladium(II) hexafluorophosphate (2), was synthesized and used as the highly efficient and recyclable catalyst for the Sonogashira reactions of aryl iodides and aryl bromides with several terminal acetylenes, under aerobic and CuI-free conditions. The activity loss, Pd black precipitation, and Pd leaching were not observed even after 7 runs in 2-catalyzed Sonogashira reactions using the room temperature IL of [Bmim]PF 6 as the reaction medium.
New activators for the coupling reaction of terminal alkynes with organic halides
Ahmed, Mohamed S. Mohamed,Sekiguchi, Akitoshi,Shimada, Tomohiro,Kawashima, Jun,Mori, Atsunori
, p. 327 - 330 (2005)
Cross-coupling reactions of terminal alkynes with organic halides catalyzed by palladium(0) or palladium(0)/Cu(I) take place in the presence of several activators, such as silver(I) oxide, tetrabutylammonium fluoride (TBAF), and tetrabutylammonium hydroxi
Thiol addition to aryl propargyl alcohols under mild conditions: An accelerating neighboring group effect
See Waters, Marjorie,Cowen, Jennifer A.,McWilliams, J. Christopher,Maligres, Peter E.,Askin, David
, p. 141 - 144 (2000)
Aryl alkynols provide a convenient entry into α-hydroxyketones via thiol addition followed by hydrolysis. Thiols have been added to several non- activated alkynes under mild, basic conditions. A coordinating functional group in close proximity to the triple bond facilitates this reaction.
Reusable Cu2O/PPh3/TBAB system for the cross-couplings of aryl halides and heteroaryl halides with terminal alkynes
Tang, Bo-Xiao,Wang, Feng,Li, Jin-Heng,Xie, Ye-Xiang,Zhang, Man-Bo
, p. 6294 - 6297 (2007)
(Chemical Equation Presented) An efficient and reusable Cu 2O/PPh3/TBAB (n-Bu4NBr) system for the cross-coupling reactions of aryl and heteroaryl halides with terminal alkynes has been developed. Four types of Cu2O, including bulky Cu 2O, cubic Cu2O nanoparticles, octahedral Cu2O nanoparticles, and spherical Cu2O nanoparticles, were examined, and the octahedral Cu2O nanoparticles were found to be the most effective catalyst for the reaction. In the presence of the octahedral Cu2O nanoparticles, PPh3, and TBAB, a variety of aryl and heteroaryl halides were reacted with alkynes including alkynols smoothly in moderate to good yields. Noteworthy is that the Cu2O/ PPh3/TBAB system can be recovered and reused several times without loss of any activities.
Amphiphilic ionic palladium complexes for aqueous-organic biphasic Sonogashira reactions under aerobic and CuI-free conditions
Wang, Xuezhu,Zhang, Jing,Wang, Yongyong,Liu, Ye
, p. 23 - 26 (2013)
The ionic Pd(II)-complexes of 2 (ammonium-[1-(2-hydroxyethyl)-3- methylimidazolium] bis[3-(diphenylphosphino)benzenesulfonate]- dichloropalladium(II) ([(NH4)(Hemim)][PdCl2(TPPMS) 2])) and 3 (bis[1-n-butyl-3-methylimidazolium] bis[3- (diphenylphosphino)benzenesulfonate]-dichloropalladium(II) ([Bmim] 2[PdCl2(TPPMS)2])) were synthesized and fully characterized. The single crystal X-ray diffraction analyses show that 2 and 3 are composed of the imidazolium-based cations and [PdCl2(TPPMS) 2]2 - anions. The properties of such imidazolium-based Pd-complexes of 2 and 3, in terms of the aqueous solubilities and the catalytic behaviors in water, could be dramatically varied. When 2 and 3 were applied as the precatalysts for the Sonogashira coupling of iodobenzene with phenylacetylene under aerobic and CuI-free conditions, the much higher yields of 1,2-diphenylethyne were obtained due to their amphiphilicity. The wide generality of 2 was available for aqueous-organic biphasic Sonogashira reactions.
