6272-52-2Relevant academic research and scientific papers
Analysis of the Orbital and Electrostatic Contributions to the Lone Pair-Aromatic Interaction Using Molecular Rotors
Karki, Ishwor,Li, Ping,Madukwe, Daniel O.,Shimizu, Ken D.,Tibbetts, Gabriel S.,Vik, Erik C.
supporting information, p. 8179 - 8182 (2021/11/13)
The attractive interaction between carbonyl oxygens and the π-face of aromatic surfaces was studied using N-phenylimide molecular rotors. The C=O···Ar interactions could stabilize the transition states but were half the strength of comparable C=O···C=O interactions. The C=O···Ar interaction had a significant electrostatic component but only a small orbital delocalization component.
α-Bromoacrylic Acids as C1 Insertion Units for Palladium-Catalyzed Decarboxylative Synthesis of Diverse Dibenzofulvenes
Zhang, Minghao,Deng, Wenbo,Sun, Mingjie,Zhou, Liwei,Deng, Guobo,Liang, Yun,Yang, Yuan
supporting information, p. 5744 - 5749 (2021/08/18)
Herein α-bromoacrylic acids have been employed as C1 insertion units to achieve the palladium-catalyzed [4 + 1] annulation of 2-iodobiphenyls, which provides an efficient platform for the construction of diverse dibenzofulvenes. This protocol enables the formation of double C(aryl)-C(vinyl) bonds via a C(vinyl)-Br bond cleavage and decarboxylation. It is particularly noteworthy that the method features a broad substrate scope, and various interesting frameworks, such as bridged ring, fused (hetero)aromatic ring, and divinylbenzene, can be successfully incorporated into the products.
Atmosphere-Controlled Palladium-Catalyzed Divergent Decarboxylative Cyclization of 2-Iodobiphenyls and α-Oxocarboxylic Acids
Zhou, Liwei,Sun, Mingjie,Zhou, Fengru,Deng, Guobo,Yang, Yuan,Liang, Yun
supporting information, p. 7150 - 7155 (2021/09/18)
A novel palladium-catalyzed divergent decarboxylative cyclization of 2-iodobiphenyls and α-oxocarboxylic acids utilizing the atmosphere as a controlled switch is reported. Under the protection of a nitrogen atmosphere, tribenzotropones are synthesized by a [4 + 3] decarboxylative cyclization. Employing a palladium/O2 system enables a [4 + 2] decarboxylative cyclization to assemble triphenylenes. Notably, preliminary mechanistic studies indicate that the formation of triphenylenes involves a double decarboxylation.
Visible-Light-Driven Difluoromethylation of Isocyanides with S-(Difluoromethyl)diarylsulfonium Salt: Access to a Wide Variety of Difluoromethylated Phenanthridines and Isoquinolines
Chen, Jia-Yi,Li, Xin,Lin, Li-Ting,Liu, Guo-Kai,Qin, Wen-Bing,Wong, Henry N. C.,Xiong, Wei
, p. 10479 - 10487 (2020/09/23)
A highly efficient approach of visible-light-driven radical difluoromethylation of isocyanides to access a wide variety of difluoromethylated phenanthridines and isoquinolines is herein described. Electrophilic S-(difluoromethyl)diarylsulfonium salt proved to be a good difluoromethyl radical precursor under photoredox catalysis. A broad range of isocyanides were tolerated to furnish the corresponding difluoromethylated phenanthridines, isoquinolines, furo[3,2-c]pyridine, and pyrido[3,4-b]indole in moderate to excellent yields under mild conditions. A plausible mechanism was also proposed.
TfOH-Promoted Transition-Metal-Free Cascade Trifluoroethylation/Cyclization of Organic Isothiocyanates by Phenyl(2,2,2-trifluoroethyl)iodonium Triflate
Zhao, Cheng-Long,Han, Qiu-Yan,Zhang, Cheng-Pan
supporting information, p. 6480 - 6484 (2018/10/09)
An efficient and transition-metal-free method for the synthesis of the structurally diversified trifluoroethylthiol phenanthridines and 3,4-dihydroisoquinolines is described. Various 2-isothiocyanobiaryls and aryl alkyl isothiocyanates reacted with phenyl(2,2,2-trifluoroethyl)iodonium triflate in CH2Cl2 in the presence of trifluoromethanesulfonic acid at 40 °C to form the corresponding trifluoroethylation/cyclization products in good to quantitative yields. This work represents the first construction of trifluoroethylthiol phenanthridine and isoquinoline derivatives from isothiocyanates in the absence of transition-metal catalysts by a one-pot procedure.
Cyclization of 2-Biphenylthiols to Dibenzothiophenes under PdCl2/DMSO Catalysis
Zhang, Tao,Deng, Guigang,Li, Hanjie,Liu, Bingxin,Tan, Qitao,Xu, Bin
supporting information, p. 5439 - 5443 (2018/09/13)
A palladium-catalyzed synthesis of dibenzothiophenes from 2-biphenylthiols is described. This highly efficient reaction employs a simple PdCl2/DMSO catalytic system, in which PdCl2 is the sole metal catalyst and DMSO functions as an oxidant and solvent. This transformation has broad substrate scope and operational simplicity and proceeds in high yield. The synthetic utility was demonstrated by the facile synthesis of helical dinapthothiophene 3 and an eminent organic semiconductor DBTDT 4. Importantly, highly strained trithiasumanene 5, a buckybowl of considerable synthetic challenge, was observed under this catalytic system.
Iron-Catalyzed Intramolecular C(sp2)-H Amination
Alt, Isabel T.,Plietker, Bernd
supporting information, p. 1519 - 1522 (2016/02/14)
The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular C-H amination of α-azidobiaryls and (azidoaryl)alkenes into the corresponding carbazoles and indoles, respectively, under mild conditions and with low catalyst loadings. These features and the broad functional-group tolerance render this method a particularly attractive alternative to established noble-metal-based procedures.
O-(Trialkylstannyl)anilines and their utility in Migita-Kosugi-Stille cross-coupling: Direct introduction of the 2-aminophenyl substituent
Izgu, Enver Cagri,Hoye, Thomas R.
supporting information, p. 4938 - 4941 (2012/11/07)
We have developed shelf- and air-stable ortho-stannylated aniline reagents that can directly be coupled with alkenyl and aryl halides via Migita-Kosugi-Stille cross-coupling. We report (i) the efficient preparation of o-(tributylstannyl)aniline (2a) and o-(trimethylstannyl)aniline (2b), (ii) the comparison of the reactivities of 2a and 2b with those of related organostannanes in cross-coupling reaction with an alkenyl halide, and (iii) the cross-coupling of 2a and 2b with a series of arylhalides and triflate.
Investigations on the 1-(2-biphenyl)piperazine motif: Identification of new potent and selective ligands for the serotonin7 (5-HT7) receptor with agonist or antagonist action in vitro or ex vivo
Lacivita, Enza,Patarnello, Daniela,Stroth, Nikolas,Caroli, Antonia,Niso, Mauro,Contino, Marialessandra,De Giorgio, Paola,Di Pilato, Pantaleo,Colabufo, Nicola A.,Berardi, Francesco,Perrone, Roberto,Svenningsson, Per,Hedlund, Peter B.,Leopoldo, Marcello
supporting information; experimental part, p. 6375 - 6380 (2012/10/08)
Here we report the design, synthesis, and 5-HT7 receptor affinity of a set of 1-(3-biphenyl)- and 1-(2-biphenyl)piperazines. The effect on 5-HT7 affinity of various substituents on the second (distal) phenyl ring was analyzed. Several compounds showed 5-HT7 affinities in the nanomolar range and >100-fold selectivity over 5-HT1A and adrenergic α1 receptors. 1-[2-(4-Methoxyphenyl)phenyl] piperazine (9a) showed 5-HT7 agonist properties in a guinea pig ileum assay but blocked 5-HT-mediated cAMP accumulation in 5-HT7- expressing HeLa cells.
ISOFORM-SELECTIVE HDAC INHIBITORS
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Page/Page column 45, (2008/06/13)
One aspect of the invention relates to isoform-selective HDAC inhibitors. Also provided are methods of sensitizing a cancer cell to the cytotoxic effects of radiotherapy. The invention also provides methods for treating cancer, methods for treating neurological diseases and methods for treating malaria. Additionally, the invention provides pharmaceutical compositions comprising an HDAC inhibitor of the invention; and kits comprising a an HDAC inhibitor of the invention.
