4226-59-9Relevant academic research and scientific papers
Pd(II)-Catalyzed CC Bond Cleavage by a Formal Group-Exchange Reaction
Ye, Runyou,Zhu, Maoshuai,Yan, Xufei,Long, Yang,Xia, Ying,Zhou, Xiangge
, p. 8678 - 8683 (2021/07/26)
A chelation-assisted palladium-catalyzed CC bond cleavage of α, β-unsaturated ketone to form alkenyl nitrile in the presence of nitrile is disclosed on the basis of a formal group-exchange reaction formulated as C1C2 + C3 → C1C3 + C2, differing from normal alkene oxidative cleavage and metathesis type. The isolated key active Pd(II) complex as well as deuterium-labeled experiment revealed the necessity of the chelation group, and a plausible catalytic pathway was proposed.
PROTEIN LABELLING
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Paragraph 0173-0174, (2021/09/26)
A process for labelling a target protein, such as a target enzyme, such as a deubiquitinating enzyme (DUB). The process comprises providing a probe-protein complex comprising a probe and the target protein. The probe comprises a recognition element and a
Copper catalyzed reduction of azides with diboron under mild conditions
Chen, Yang,Deng, Shengqi,Gao, Yihua,Liu, Liwen,Liu, Yu,Lu, Da,Wang, Qianwen,Zhang, Xiao
supporting information, (2020/02/27)
We report herein the first Cu catalyzed reduction of azides with B2pin2 (pin = pinacolato) as the reductant under very mild conditions. A series of primary amines and amides were obtained in moderate to excellent yields with high chemoselectivity and good functional group tolerance. This reaction can be performed with a cheap copper salt, a simple NHC ligand and a diboron reagent.
Copper-Catalyzed Aerobic Oxidation of Amines to Benzothiazoles via Cross Coupling of Amines and Arene Thiolation Sequence
Kim, Jihyeon,Oh, Kyungsoo
supporting information, p. 3576 - 3582 (2020/08/05)
A one-pot three-component synthesis of benzothiazoles has been developed using the copper-catalyzed aerobic cross coupling of amines followed by arene thiolation using elemental sulfur. The dual roles of elemental sulfur and CuCl(OH)-TMEDA in the aerobic amine oxidation and the aniline thiolation enable the facile access to benzothiazole derivatives from readily available starting materials. The operational simplicity of the current promiscuous catalyst system suggests the high synthetic potential in the preparation of heterocyclic compounds. (Figure presented.).
Highly chemoselective, sterically sensitive NHC-catalysed amine acylation with pyridil
Maguire, Amy C.,Kumar, Vikas,Connon, Stephen J.
supporting information, p. 13526 - 13529 (2019/11/14)
A new strategy for the protection of amines has been developed involving reaction with pyridil under the influence of N-heterocyclic carbene catalysis. The methodology is capable of distinguishing between two amines characterised by small differences in steric bulk and the resulting pyridoyl amides can be cleaved without requiring either strongly acidic or basic hydrolysis.
Structural Basis for Achieving GSK-3β Inhibition with High Potency, Selectivity, and Brain Exposure for Positron Emission Tomography Imaging and Drug Discovery
Bernard-Gauthier, Vadim,Mossine, Andrew V.,Knight, Ashley,Patnaik, Debasis,Zhao, Wen-Ning,Cheng, Chialin,Krishnan, Hema S.,Xuan, Lucius L.,Chindavong, Peter S.,Reis, Surya A.,Chen, Jinshan Michael,Shao, Xia,Stauff, Jenelle,Arteaga, Janna,Sherman, Phillip,Salem, Nicolas,Bonsall, David,Amaral, Brenda,Varlow, Cassis,Wells, Lisa,Martarello, Laurent,Patel, Shil,Liang, Steven H.,Kurumbail, Ravi G.,Haggarty, Stephen J.,Scott, Peter J. H.,Vasdev, Neil
supporting information, p. 9600 - 9617 (2019/10/28)
Using structure-guided design, several cell based assays, and microdosed positron emission tomography (PET) imaging, we identified a series of highly potent, selective, and brain-penetrant oxazole-4-carboxamide-based inhibitors of glycogen synthase kinase-3 (GSK-3). An isotopologue of our first-generation lead, [3H]PF-367, demonstrates selective and specific target engagement in vitro, irrespective of the activation state. We discovered substantial ubiquitous GSK-3-specific radioligand binding in Tg2576 Alzheimer's disease (AD), suggesting application for these compounds in AD diagnosis and identified [11C]OCM-44 as our lead GSK-3 radiotracer, with optimized brain uptake by PET imaging in nonhuman primates. GSK-3β-isozyme selectivity was assessed to reveal OCM-51, the most potent (IC50 = 0.030 nM) and selective (>10-fold GSK-3β/GSK-3α) GSK-3β inhibitor known to date. Inhibition of CRMP2T514 and tau phosphorylation, as well as favorable therapeutic window against WNT/β-catenin signaling activation, was observed in cells.
Organocatalytic Synthesis of Oxazolines and Dihydrooxazines from Allyl-Amides: Bypassing the Inherent Regioselectivity of the Cyclization
Theodorou, Alexis,Triandafillidi, Ierasia,Kokotos, Christoforos G.
, p. 951 - 957 (2018/01/22)
A selective and efficient methodology for the construction of either oxazolines or dihydrooxazines from the corresponding allyl-amides is reported. Bypassing the inherent selectivity of the cyclization and depending on the substitution pattern of the substrate, a selective epoxidation-cyclization was developed leading to either the five-membered or the six-membered ring, upon simple and complementary reaction conditions. The cyclization products were obtained in good to excellent yields and high selectivities. (Figure presented.).
Practical regio- and stereoselective azidation and amination of terminal alkenes
Ojo, Olatunji S.,Miranda, Octavio,Baumgardner, Kyle C.,Bugarin, Alejandro
supporting information, p. 9354 - 9358 (2019/01/03)
There is significant interest in developing more rapid and efficient production of nitrogen-containing allylic compounds, as widely used in various syntheses. This work reports a variety of allylic azides and allylic amines synthesized by an efficient, new one-pot protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear (E)-isomer, under metal-free conditions. This process tolerates several functional groups including halogen-containing molecules; it is general for azides and amine nucleophiles; and, adducts were obtained in good yields.
Catalytic Diastereo- and Enantioselective Fluoroamination of Alkenes
Mennie, Katrina M.,Banik, Steven M.,Reichert, Elaine C.,Jacobsen, Eric N.
supporting information, p. 4797 - 4802 (2018/04/17)
The stereoselective synthesis of syn-β-fluoroaziridine building blocks via chiral aryl iodide-catalyzed fluorination of allylic amines is reported. The method employs HF-pyridine as a nucleophilic fluoride source together with mCPBA as a stoichiometric oxidant, and affords access to arylethylamine derivatives featuring fluorine-containing stereocenters in high diastereo- and enantioselectivity. Catalyst-controlled diastereoselectivity in the fluorination of chiral allylic amines enabled the preparation of highly enantioenriched 1,3-difluoro-2-amines bearing three contiguous stereocenters. The enantioselective catalytic method was applied successfully to other classes of multifunctional alkene substrates to afford anti-β-fluoropyrrolidines, as well as a variety of 1,2-oxyfluorinated products.
Direct use of allylic alcohols and allylic amines in palladium-catalyzed allylic amination
Jing, Jiangyan,Huo, Xiaohong,Shen, Jiefeng,Fu, Jingke,Meng, Qinghua,Zhang, Wanbin
supporting information, p. 5151 - 5154 (2017/07/12)
Allylic alcohols and allylic amines were directly utilized in a Pd-catalyzed hydrogen-bond-activated allylic amination under mild reaction conditions in the absence of any additives. The cooperative action of a Pd-catalyst and a hydrogen-bonding solvent is most likely responsible for its high reactivity. The catalytic system is compatible with a variety of functional groups and can be used to prepare a wide range of linear allylic amines in good to excellent yields. Furthermore, this methodology can be easily applied to the one-step synthesis of two drugs, cinnarizine and naftifine, on a gram scale.
