cas 17061-62-0, BIS-(4-METHOXY-BENZYL)-AMINE

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Synthesis, spectral, crystal structures, Hirshfeld surface analysis and DFT studies on bis(N,N-di(4-methoxybenzyl)dithiocarbamato-S,S′)zinc(II) and its imine adducts: new precursor for the preparation of hexagonal ZnS
[Zn(4-mbzdtc)2] (1), [Zn(4-mbzdtc)2(py)] (2), [Zn2(4-mbzdtc)4(4,4′-bipy)] (3), and [Zn(4-mbzdtc)2(2,2′-bipy)] (4), (where, 4-mbzdtc = N,N-di(4-methoxybenzyl)dithiocarbamate) were prepared and characte
Selvaganapathi, Pandurangan,Thirumaran, Subbiah,Ciattini, Samuele
p. 655 - 667
(2017)
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Switching Selectivity in Copper-Catalyzed Transfer Hydrogenation of Nitriles to Primary Amine-Boranes and Secondary Amines under Mild Conditions
A simple and efficient copper-catalyzed selective transfer hydrogenation of nitriles to primary amine-boranes and secondary amines with an oxazaborolidine-BH3 complex is reported. The selectivity control was achieved under mild conditions by switching the solvent and the copper catalysts. More than 30 primary amine-boranes and 40 secondary amines were synthesized via this strategy in high selectivity and yields of up to 95%. The strategy was applied to the synthesis of 15N labeled in 89% yield.
Song, Hao,Xiao, Yao,Zhang, Zhuohua,Xiong, Wanjin,Wang, Ren,Guo, Liangcheng,Zhou, Taigang
p. 790 - 800
(2022/01/11)

Aluminum Metal-Organic Framework-Ligated Single-Site Nickel(II)-Hydride for Heterogeneous Chemoselective Catalysis
The development of chemoselective and heterogeneous earth-abundant metal catalysts is essential for environmentally friendly chemical synthesis. We report a highly efficient, chemoselective, and reusable single-site nickel(II) hydride catalyst based on robust and porous aluminum metal-organic frameworks (MOFs) (DUT-5) for hydrogenation of nitro and nitrile compounds to the corresponding amines and hydrogenolysis of aryl ethers under mild conditions. The nickel-hydride catalyst was prepared by the metalation of aluminum hydroxide secondary building units (SBUs) of DUT-5 having the formula of Al(μ2-OH)(bpdc) (bpdc = 4,4′-biphenyldicarboxylate) with NiBr2 followed by a reaction with NaEt3BH. DUT-5-NiH has a broad substrate scope with excellent functional group tolerance in the hydrogenation of aromatic and aliphatic nitro and nitrile compounds under 1 bar H2 and could be recycled and reused at least 10 times. By changing the reaction conditions of the hydrogenation of nitriles, symmetric or unsymmetric secondary amines were also afforded selectively. The experimental and computational studies suggested reversible nitrile coordination to nickel followed by 1,2-insertion of coordinated nitrile into the nickel-hydride bond occurring in the turnover-limiting step. In addition, DUT-5-NiH is also an active catalyst for chemoselective hydrogenolysis of carbon-oxygen bonds in aryl ethers to afford hydrocarbons under atmospheric hydrogen in the absence of any base, which is important for the generation of fuels from biomass. This work highlights the potential of MOF-based single-site earth-abundant metal catalysts for practical and eco-friendly production of chemical feedstocks and biofuels.
Antil, Neha,Kumar, Ajay,Akhtar, Naved,Newar, Rajashree,Begum, Wahida,Dwivedi, Ashutosh,Manna, Kuntal
p. 3943 - 3957
(2021/04/12)

Platinum Nanoparticles Uniformly Dispersed on Covalent Organic Framework Supports for Selective Synthesis of Secondary Amines
Covalent organic frameworks (COFs) with pore structures are talented supports for active components. In this report, COF has been rationally fabricated and served as host for growing uniformly dispersed platinum nanoparticles with a narrow size distribution (2 nm). The obtained hybrid Pt/COF exhibits high catalytic activity in the reductive amination of benzaldehyde towards secondary amines with a yield of 96 % and good recyclability. The preferable selectivity towards secondary amines could be attributed to synergistic effects of active platinum nanoparticles and COF, in which metallic Pt nanoparticles were uniformly dispersed with a positively charged surface. This work will open an avenue towards controlling the interaction between active metals and support as well as rational design of catalysts for demanding transformations for fine agrochemicals intermediates.
Li, Xinjun,Liu, Jianguo,Ma, Longlong,Tang, Long,Wang, Chenguang,Wang, Nan
(2022/01/22)

Photo-Electroswitchable Arylaminoazobenzenes
Azobenzenes appended with a redox-active arylamino group (redox auxiliary, RA) are prepared and shown to undergo fast, complete, and catalytic Z→E azo isomerization upon electron loss from the RA unit of the azobenzene. The RA-azo structures can be reversibly (E→Z→E)n cycled by sequential photo- and electrostimulation. Due to the robust nature of the RA?+-azo radical cation chain carrying species, initiation of electron transfer (ET) catalysis occurs at low levels (1.0-0.04 mol %) of catalytic loading and is effective even at Z-RA-azo concentrations of 10-4-10-5 M, yielding TONs (turnover numbers) of 100-2300 under such dilute conditions. The RA-azo Z→E conversion is demonstrated using chemical oxidation (redox switching), electrochemical oxidation (electro switching), and photochemical oxidation (photoredox switching). The Z→E acceleration is shown to be at least 2 × 109-fold for RA-azo 5. DFT calculations on methyl yellow suggest that a N-centered radical cation of the RA group stabilizes the Z→E N-N twist transition state of the RA?+-azo, yielding a large reduction in the barrier for RA?+-azo compared to neutral RA-azo. The RA-azo structure class has nanomechanical features that can be toggled with photo- and electrostimulation, the latter offering a quick switch for complete Z→E conversion.
Saint-Louis, Carl Jacky,Warner, David J.,Keane, Katie S.,Kelley, Melody D.,Meyers, Connor M.,Blackstock, Silas C.
p. 11341 - 11353
(2021/08/24)

Selective Synthesis of Symmetrical Secondary Amines from Nitriles with a Pt?CuFe/Fe3O4 Catalyst and Ammonia Borane as Hydrogen Donor
Hydrogenation of nitriles is an efficient and environmentally friendly route to synthesize symmetrical secondary amines, but it usually produces a mixture of amines, imines, and hydrogenolysis by-products. Herein we report a magnetic quaternary-component Pt?CuFe/Fe3O4 nanocatalyst system for the selective synthesis of symmetrical secondary amines with ammonia borane as hydrogen donor. The catalyst with a low Pt loading (0.456 wt%) is the source of the activity, and the d-band electron transfer from Cu to Fe enhances the selectivity. This synergistic effect results in the transformation of benzonitrile to dibenzylamine with excellent conversion (up to 99 %) and nearly quantitative selectivity (up to 96 %) under mild reaction conditions, nevertheless, the reaction TOF is as high as up to 1409.9 h?1. A variety of nitriles are suitable for the synthesis of symmetrical secondary amines. More importantly, unwanted hydrogenolysis byproducts, especially toluene, is not detected at all. In addition, the catalyst is magnetically recoverable, and it can be reused up to five times.
Ai, Yongjian,Guo, Rongxiu,He, GuangQi,Hu, Ze-nan,Liang, Qionglin,Liu, Lei,Niu, Dun,Sun, Hong-bin,Tian, Haimeng,Zhang, Xinyue
p. 1783 - 1788
(2020/09/02)

Discovery of novel VX-809 hybrid derivatives as F508del-CFTR correctors by molecular modeling, chemical synthesis and biological assays
Cystic fibrosis (CF) is the autosomal recessive disorder most recurrent in Caucasian populations. It is caused by different mutations in the cystic fibrosis transmembrane regulator protein (CFTR) gene, with F508del being the most common. During the last y
Parodi, Alice,Righetti, Giada,Pesce, Emanuela,Salis, Annalisa,Tasso, Bruno,Urbinati, Chiara,Tomati, Valeria,Damonte, Gianluca,Rusnati, Marco,Pedemonte, Nicoletta,Cichero, Elena,Millo, Enrico
(2020/10/02)

Selective Synthesis of Secondary Amines from Nitriles by a User-Friendly Cobalt Catalyst
Selective hydrogenation/reductive amination of nitriles to secondary amines catalyzed by an inexpensive and user-friendly cobalt complex, (Xantphos)CoCl2, is reported. The use of (Xantphos)CoCl2 and ammonia borane (NH3?BH3) combination affords the selective reduction of nitriles to symmetrical secondary amines, whereas the employment of (Xantphos)CoCl2 and dimethylamine borane (Me2NH?BH3) along with external amines produce unsymmetrical secondary amines and tertiary amines. The general applicability of this methodology is demonstrated by the synthesis of 43 symmetrical and unsymmetrical secondary and tertiary amines bearing diverse functionalities. (Figure presented.).
Sharma, Dipesh M.,Punji, Benudhar
supporting information
p. 3930 - 3936
(2019/07/12)

An intramolecular C(sp3)-H imination using PhI-m CPBA
Herein, a highly exothermic primary amine-polyvalent iodine reaction has been used successfully for selective functionalization of acidic C(sp3)-H groups for a dehydrogenative C-H imination reaction by 4H elimination. Overall, C(sp3)-H imination at 1,5 distances was readily done via organocatalysis using PhI (10 mol%)-mCPBA under ambient conditions.
Bose, Anima,Maiti, Saikat,Sau, Sudip,Mal, Prasenjit
p. 2066 - 2069
(2019/02/19)

SUBSTITUTED PYRIMIDINONES AS AGONISTS OF THE APJ RECEPTOR
Compounds of Formula I and Formula II, pharmaceutically acceptable salts thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and may have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the following structures: Figure I and Figure II where the definitions of the variables are provided herein.
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(2019/11/19)

FUSED TRIAZOLE AGONISTS OF THE APJ RECEPTOR
Compounds of Formula I, pharmaceutically acceptable salts thereof, tautomers thereof, pharmaceutically acceptable salts of the tautomers, or mixtures thereof are agonists of the APJ Receptor and may have use in treating cardiovascular and other conditions. Compounds of Formula (I) have the following structure: where the definitions of the variables are provided herein.
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Paragraph 0237

(2019/05/22)

Iron-Catalyzed Intramolecular C-H Amination of α-Azidyl Amides
Iron-catalyzed intramolecular C-H amination of aliphatic azides has recently emerged as a powerful tool for the preparation of nitrogen heterocycles. This paper reports that α-azidyl amides can be converted in high efficacy to imidazolinone compounds via intramolecular C(sp3)-H amination by the action of a simple catalytic system composed of FeCl2 and a β-diketiminate ligand. The reactions provide a simple and atom-economical approach toward polysubstituted imidazolinones.
Zhao, Xiaopeng,Liang, Siyu,Fan, Xing,Yang, Tonghao,Yu, Wei
supporting information
p. 1559 - 1563
(2019/03/20)

Electrochemical Approach for Direct C-H Phosphonylation of Unprotected Secondary Amine
Direct α-phosphonylation of an unprotected secondary amine in a single step is of practical importance to amino phophophates. However, this protocol is limited due to the high redox barrier of unprotected amine. In this paper, we report C-H phosphonylation of an unprotected secondary amine via an electrochemical approach in the presence of catalytic carboxylate salt. This metal-free and exogenous oxidant-free method furnishes diverse target molecules with satisfactory yield under mild reaction conditions. Successful application of the protocol in a gram-scale experiment demonstrates the potential utility for further functionalization.
Huang, Min,Dai, Jie,Cheng, Xu,Ding, Mengning
supporting information
p. 7759 - 7762
(2019/10/11)

Pd/TiO2-Photocatalyzed Self-Condensation of Primary Amines to Afford Secondary Amines at Ambient Temperature
Symmetric secondary amines were synthesized by the self-condensation of primary amines over a palladium-loaded titanium dioxide (Pd/TiO2) photocatalyst. The reactions afforded a series of secondary amines in moderate to excellent isolated yields at ambient temperature (30 °C, in cyclopentyl methyl ether). Applicability for one-pot pharmaceutical synthesis was demonstrated by a photocatalytic reaction sequence of self-condensation of an amine followed by N-alkylation of the resulting secondary amine with an alcohol.
Wang, Lyu-Ming,Kobayashi, Kensuke,Arisawa, Mitsuhiro,Saito, Susumu,Naka, Hiroshi
supporting information
p. 341 - 344
(2018/12/11)

A highly active worm-like PtMo nanowire for the selective synthesis of dibenzylamines
Worm-like nanowires are among the most active nanomaterials. In this study, we report the synthesis of dibenzylamine (DBA) motifs from reductive amination of either aldehydes or nitriles catalyzed by entirely new worm-like PtMo nanowires (PtMo WNWs). Under the assistance of H2 gas, PtMo WNWs can be prepared in a facile manner, following which, their structure and composition are characterized by TEM, XRD, XPS, etc. Upon careful optimization of reaction parameters, the as-prepared PtMo WNWs work effectively in the activation of dihydrogen molecules, and both aldehydes and nitriles can be used as starting materials to fabricate DBAs under mild and green conditions. The reaction kinetics has been investigated, which reveals that the PtMo WNWs show superior activity in the conversion of imines into amines. This study provides a practical advancement in the preparation of amines. Moreover, the protocol reported herein is feasible for the synthesis of worm-like nanostructures with designed composition for various catalytic applications.
Lu, Shuanglong,Xu, Pengyao,Cao, Xueqin,Gu, Hongwei
p. 8755 - 8760
(2018/03/08)

Chemoselective hydrogenation of nitriles to secondary or tertiary amines catalyzed by aqueous-phase catalysts supported on hexagonal mesoporous silica
The first supported aqueous-phase catalyst for the hydrogenation of nitriles is revealed. The catalyst prepared from Pd(PhCN)2Cl2, water-soluble ligand 2,2′-biquinoline-4,4′-dicarboxylic acid dipotassium salt and mesoporous silica is a highly efficient catalyst for the selective formation of secondary or tertiary amines from aromatic or aliphatic nitriles. The catalytic system is stable and can be recycled and reused three times without loss of activity and selectivity. This environmentally friendly process is, in addition, an attractive alternative to many homogeneous and heterogeneous catalysts because of its easy preparation and the moderate operational conditions under which it is highly active.
Nait Ajjou, Abdelaziz,Robichaud, André
(2018/09/12)

HETEROARYL-SUBSTITUTED TRIAZOLES AS APJ RECEPTOR AGONISTS
Compounds of Formula (I) and Formula (II), pharmaceutically acceptable salt thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and may have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the following structures: where the definitions of the variables are provided herein.
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Paragraph 0795

(2018/06/12)

CYCLOALKYL SUBSTITUTED TRIAZOLE COMPOUNDS AS AGONISTS OF THE APJ RECEPTOR
Compounds of Formula I and Formula II, pharmaceutically acceptable salt thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and may have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the following structures:(I) (II) where the definitions of the variables are provided herein.
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Paragraph 0305

(2018/06/06)

TRIAZOLE PHENYL COMPOUNDS AS AGONISTS OF THE APJ RECEPTOR
Compounds of Formula I and Formula II, pharmaceutically acceptable salt thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and may have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the following structures: (I), (II) where the definitions of the variables are provided herein.
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Paragraph 0351

(2018/06/06)

TRIAZOLE FURAN COMPOUNDS AS AGONISTS OF THE APJ RECEPTOR
Compounds of Formula (I) and Formula (II), pharmaceutically acceptable salt thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and have use in treating cardiovascular and other conditions. Compounds of Formula (I) and Formula (II) have the following structures: (I); (II). Intermediates (V) are also claimed.
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Paragraph 0248; 0762; 0763

(2018/06/12)

TRIAZOLE PYRIDYL COMPOUNDS AS AGONISTS OF THE APJ RECEPTOR
Compounds of Formula I and Formula II, pharmaceutically acceptable salt thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and may have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the structures where the definitions of the variables are provided herein.
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Paragraph 0279

(2018/06/06)

COMPOUNDS THAT INHIBIT MCL-1 PROTEIN
Provided herein are myeloid cell leukemia 1 protein (Mcl-1) inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula (I), or a stereoisomer thereof; and pharmaceutically acceptable salts thereof and pharmaceutical compositions containing the compounds. The compounds and compositions provided herein may be used, for example, in the treatment of diseases or conditions, such as cancer.
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Page/Page column 810

(2018/10/25)

ALKYL SUBSTITUTED TRIAZOLE COMPOUNDS AS AGONISTS OF THE APJ RECEPTOR
Compounds of Formula I and Formula II, pharmaceutically acceptable salt thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and may have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the following structures: (I), (II) where the definitions of the variables are provided herein.
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Paragraph 0298

(2018/06/06)

Conversion of Primary Amines to Symmetrical Secondary and Tertiary Amines using a Co-Rh Heterobimetallic Nanocatalyst
Symmetrical tertiary amines have been efficiently realized from amine and secondary amines via deaminated homocoupling with heterogeneous bimetallic Co2Rh2/C as catalyst (molar ratio Co:Rh=2:2). Unsymmetric secondary anilines were produced from the reaction of anilines with symmetric tertiary amines. The Co2Rh2/C catalyst exhibited very high catalytic activity towards a wide range of amines and could be conveniently recycled ten times without considerable leaching. (Figure presented.).
Chung, Hyunho,Han, Seulgi,Chung, Young Keun,Park, Ji Hoon
supporting information
p. 1267 - 1272
(2018/02/12)

Synthesis of Symmetric and Unsymmetric Secondary Amines from the Ligand-Promoted Ruthenium-Catalyzed Deaminative Coupling Reaction of Primary Amines
The catalytic system generated in situ from the tetranuclear Ru-H complex with a catechol ligand (1/L1) was found to be effective for the direct deaminative coupling of two primary amines to form secondary amines. The catalyst 1/L1 was highly chemoselective for promoting the coupling of two different primary amines to afford unsymmetric secondary amines. The analogous coupling of aniline with primary amines formed aryl-substituted secondary amines. The treatment of aniline-d7 with 4-methoxybenzylamine led to the coupling product with significant deuterium incorporation on CH2 (18% D). The most pronounced carbon isotope effect was observed on the α-carbon of the product isolated from the coupling reaction of 4-methoxybenzylamine (C(1) = 1.015(2)). A Hammett plot was constructed from measuring the rates of the coupling reaction of 4-methoxyaniline with a series of para-substituted benzylamines 4-X-C6H4CH2NH2 (X = OMe, Me, H, F, CF3) (ρ = -0.79 ± 0.1). A plausible mechanistic scheme has been proposed for the coupling reaction on the basis of these results. The catalytic coupling method provides an operationally simple and chemoselective synthesis of secondary amine products without using any reactive reagents or forming wasteful byproducts.
Arachchige, Pandula T. Kirinde,Lee, Hanbin,Yi, Chae S.
p. 4932 - 4947
(2018/05/08)

Cobalt complex, preparation method thereof, and application thereof in selective catalysis of transfer hydrogenation reaction of cyano group
The invention discloses a cobalt complex, a preparation method thereof, and an application thereof in the selective catalysis of a transfer hydrogenation reaction of a cyano group. The structural formula of the cobalt complex is represented by formula I. The cobalt complex is prepared through a reaction of a cobalt salt and an NNP ligand or a PNP ligand under the protection of an inert atmosphere;and the chemical formula of the cobalt salt is CoX12, wherein X1 represents halogen, a sulfate radical, a perchlorate radical, a hexafluorophosphate radical, a hexafluoroantimonate radical, a tetrafluoroborate radical, a trifluoromethanesulfonate radical or a tetra(pentafluorophenyl)borate radical. The cobalt complex can be used in the selective catalysis of the transfer hydrogenation reaction ofthe cyano group to obtain a primary amine compound, a secondary amine compound and a tertiary amine compound, the primary amine compound, the secondary amine compound and the tertiary amine compoundare important intermediates in a series of subsequent functionalizing reactions, and the cobalt complex has a very high catalysis activity, and has great research values and a great application prospect.
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Paragraph 0165-0168

(2018/05/07)

Catalyst-Dependent Selective Hydrogenation of Nitriles: Selective Synthesis of Tertiary and Secondary Amines
In the presence of palladium on carbon (Pd/C) as a catalyst, hydrogenation of aliphatic nitriles in cyclohexane efficiently proceeded at 25-60 °C under ordinary hydrogen gas pressure to afford the corresponding tertiary amines. However, the use of rhodium on carbon (Rh/C) led to the highly selective generation of secondary amines. Hydrogenation of aromatic nitriles and cyclohexanecarbonitrile selectively produced secondary amines in the presence of either Pd/C or Rh/C.
Monguchi, Yasunari,Mizuno, Masahiro,Ichikawa, Tomohiro,Fujita, Yuki,Murakami, Eri,Hattori, Tomohiro,Maegawa, Tomohiro,Sawama, Yoshinari,Sajiki, Hironao
p. 10939 - 10944
(2017/10/27)

Nano-sized La0.5Ca0.5CoO3-mediated reduction by nabh4 of aryl nitriles to bis-(benzyl) amines
Nano-sized La0.5Ca0.5CoO3 perovskite, which was produced via the sol-gel method, was an efficient heterogeneous catalyst in combination with NaBH4 for the rapid chemoselective reduction of aryl nitriles to bis-(benzyl)amines at 40°C in good to excellent yields. The physico-chemical properties of the catalyst were characterized by means of differential thermal analysis (DTA), thermogravimetric analysis (TGA), X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive spectroscopy (EDX) and particle size distributions images. The results show that nanoparticles have regular shapes with well-defined crystal faces with an average size of 30 nm.
Bavandi, Hossein,Shiri, Ali,Tavakkoli, Haman
p. 3330 - 3334
(2017/05/29)

Triazolylidene-Iridium Complexes with a Pendant Pyridyl Group for Cooperative Metal–Ligand Induced Catalytic Dehydrogenation of Amines
Two iridium(III) complexes containing a C,N-bidentate pyridyl-triazolylidene ligand were prepared that are structurally very similar but differ in their pendant substituent. Whereas complex 1 contains a non-coordinating pyridyl unit, complex 2 has a phenyl group on the triazolylidene substituent. The presence of the basic pyridyl unit has distinct effects on the catalytic activity of the complex in the oxidative dehydrogenation of benzylic amines, inducing generally higher rates, higher selectivity towards formation of imines versus secondary amines, and notable quantities of tertiary amines when compared to the phenyl-functionalized analogue. The role of the pyridyl functionality has been elucidated from a set of stoichiometric experiments, which demonstrate hydrogen bonding between the pendant pyridyl unit and the amine protons of the substrate. Such Npyr???H?N interactions are demonstrated by X-ray diffraction analysis, 1H NMR, and IR spectroscopy, and suggest a pathway of substrate bond-activation that involves concerted substrate binding through the Lewis acidic iridium center and the Lewis basic pyridyl site appended to the triazolylidene ligand, in agreement with ligand–metal cooperative substrate activation.
Valencia, Marta,Pereira, Ana,Müller-Bunz, Helge,Belderraín, Tomás R.,Pérez, Pedro J.,Albrecht, Martin
p. 8901 - 8911
(2017/07/11)

COMPOUNDS THAT INHIBIT MCL-1 PROTEIN
Provided herein are myeloid cell leukemia 1 protein (Mcl-1) inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula I, and pharmaceutically acceptable salts thereof and pharmaceutical compositions containing the compounds. The compounds and compositions provided herein may be used, for example, in the treatment of diseases or conditions, such as cancer.
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Page/Page column 143; 144; 617; 1975; 1976

(2017/09/15)

Rational design, synthesis, and structure–activity relationships of 5-amino-1H-pyrazole-4-carboxylic acid derivatives as protein tyrosine phosphatase 1B inhibitors
A series of novel amino-carboxylic based pyrazole as protein tyrosine phosphatase 1B (PTP1B) inhibitors were designed on the basis of structure-based pharmacophore model and molecular docking. Compounds containing different hydrophobic tail (1,2-diphenyl ethanone, oxdiadizole and dibenzyl amines) were synthesized and evaluated in PTP1B enzymatic assay. Structure–activity relationship based optimization resulted in identification of several potent, metabolically stable and cell permeable PTP1B inhibitors.
Basu, Sujay,Prathipati, Philip,Thorat, Sachin,Ansari, Shariq,Patel, Meena,Jain, Vaibhav,Jinugu, Ramana R.,Niranjan, Sanjay,De, Siddhartha,Reddy, Satyanarayana
supporting information
p. 67 - 74
(2016/12/18)

HETEROCYCLIC TRIAZOLE COMPOUNDS AS AGONISTS OF THE APJ RECEPTOR
Compounds of Formula I and Formula II, pharmaceutically acceptable salts thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and may have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the following structures: where the definitions of the variables are provided herein.
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Paragraph 1045; 1046

(2017/12/01)

Active and Recyclable Catalytic Synthesis of Indoles by Reductive Cyclization of 2-(2-Nitroaryl)acetonitriles in the Presence of Co-Rh Heterobimetallic Nanoparticles with Atmospheric Hydrogen under Mild Conditions
A cobalt-rhodium heterobimetallic nanoparticle-catalyzed reductive cyclization of 2-(2-nitroaryl)acetonitriles to indoles has been achieved. The tandem reaction proceeds without any additives under the mild conditions (1 atm H2 and 25 °C). This procedure could be scaled up to the gram scale. The catalytic system is significantly stable under these reaction conditions and could be reused more than ten times without loss of catalytic activity.
Choi, Isaac,Chung, Hyunho,Park, Jang Won,Chung, Young Keun
p. 5508 - 5511
(2016/11/17)

Stereocontrolled Synthesis of β-Lactams within [2]Rotaxanes: Showcasing the Chemical Consequences of the Mechanical Bond
The intramolecular cyclization of N-benzylfumaramide [2]rotaxanes is described. The mechanical bond of these substrates activates this transformation to proceed in high yields and in a regio- and diastereoselective manner, giving interlocked 3,4-disubstituted trans-azetidin-2-ones. This activation effect markedly differs from the more common shielding protection of threaded functions by the macrocycle, in this case promoting an unusual and disfavored 4-exo-trig ring closure. Kinetic and synthetic studies allowed us to delineate an advantageous approach toward β-lactams based on a two-step, one-pot protocol: an intramolecular ring closure followed by a thermally induced dethreading step. The advantages of carrying out this cyclization in the confined space of a benzylic amide macrocycle are attributed to its anchimeric assistance.
Martinez-Cuezva, Alberto,Lopez-Leonardo, Carmen,Bautista, Delia,Alajarin, Mateo,Berna, Jose
p. 8726 - 8729
(2016/07/30)

Cationic Iridium and Rhodium Complexes with C-N Chelating Primary Benzylic Amine Ligands as Potent Catalysts for Hydrogenation of Unsaturated Carbon-Nitrogen Bonds
Cationic half-sandwich C-N chelating Ir and Rh complexes [Cp?M(NCCH3){2(N,C)-NH2CR2-2-C6H4}]+SbF6- (1a, M = Ir, R = CH3; 1b, M = Ir, R = C6H5; 2a, M = Rh, R = CH3; 2b, M = Rh, R = C6H5) are synthesized by AgSbF6-mediated halide abstraction from neutral azametallacycles derived from tritylamine or cumylamine and are fully characterized by NMR spectroscopy and X-ray crystallography. The treatment of the cationic complex 1b with H2 gas under ambient conditions in the presence of triethylamine in THF-d8 quantitatively yielded hydrido(amine) complex [Cp?Ir(H){2(N,C)-NH2C(C6H5)2-2-C6H4}] (4). The C-N chelating Ir complex shows a higher catalytic activity than an N-N chelating complex, [Cp?Ir(NCCH3)(Tscydn)]+SbF6- (3; Tscydn = N-(p-toluenesulfonyl)-1,2-cyclohexanediamime), that has been previously used for the asymmetric hydrogenation of acyclic imines. For example, the cationic Ir complex 1a promoted the hydrogenation of N-(1-phenylethylidene)benzylamine under 30 atm at 30 °C in the presence of excess AgSbF6 to produce the corresponding amine in 97% yield within 2 h. The cationic Rh complexes 2 serve as efficient catalysts for hydrogenative condensation of nitriles in the presence of AgSbF6, producing dibenzylamines selectively even at 60 °C.
Sato, Yasuhiro,Kayaki, Yoshihito,Ikariya, Takao
p. 1257 - 1264
(2016/06/01)

Mild and Selective Cobalt-Catalyzed Chemodivergent Transfer Hydrogenation of Nitriles
Herein, we describe a selective cobalt-catalyzed chemodivergent transfer hydrogenation of nitriles to synthesize primary, secondary, and tertiary amines. The solvent effect plays a key role for the selectivity control. The general applicability of this procedure was highlighted by the synthesis of more than 70 amine products bearing various functional groups in high chemoselectivity. Moreover, this mild system achieved >2000 TONs (turnover numbers) for the transfer hydrogenation of nitriles.
Shao, Zhihui,Fu, Shaomin,Wei, Mufeng,Zhou, Shaolin,Liu, Qiang
supporting information
p. 14653 - 14657
(2016/11/23)

Selective hydrogenation of nitriles to secondary amines catalyzed by a pyridyl-functionalized and alkenyl-tethered NHC-Ru(II) complex
A set of Co(III) and Ru(II) compounds are synthesized bearing pyridyl-functionalized and alkenyl-tethered N-heterocyclic carbene (NHC) ligand (L1). [CoIII(L1)3](PF6)3 (1) was synthesized by the reaction of [L1H]PF6, Co(OAc)2.4H2O, K2CO3 in tetrahydrofuran (THF) under refluxing condition. [RuIIL1(η6-p-cymene)Cl]PF6 (2) was synthesized via transmetallation method. For both compounds, the NHC ligand chelates the metal through carbene carbon and pyridyl nitrogen whereas the butenyl unit remains free. Compound 2 hydrogenates organic nitriles efficiently providing selectively secondary amines. In the presence of external amines, unsymmetrical secondary amines are also obtained.
Saha, Sayantani,Kaur, Mandeep,Singh, Kuldeep,Bera, Jitendra K.
p. 87 - 94
(2016/06/09)

Palladium nanoparticles stabilised by cinchona-based alkaloids in glycerol: Efficient catalysts for surface assisted processes
Palladium nanoparticles (PdNPs) were synthesised and fully characterised, both in solution and the solid state, using naturally-occurring cinchona-based alkaloids in neat glycerol. These nano-systems were stable under reaction conditions, finding applications in hydrogenation and hydrodehalogenation processes, as a result of their surface-like behaviour. Their reactivity was improved in relation to that involving PdNPs stabilised by phosphines and also by Pd/C as a heterogenous catalyst, mainly in terms of recyclability. In particular, the colloidal palladium catalyst stabilised by quinidine was highly efficient to promote the hydrodechlorination of aromatic compounds under low dihydrogen pressure. These original catalysts found applications in the synthesis of secondary and tertiary amines including N-substituted anilines, by means of one-pot tandem Pd-catalysed methodologies under smooth conditions. In all of these processes, glycerol performed a crucial function as a liquid support for the immobilisation of nanoparticle-based catalysts, allowing both the stabilisation of the nano-catalysts and easy recycling of the catalytic phase.
Reina,Pradel,Martin,Teuma,Gómez
p. 93205 - 93216
(2016/10/11)

TRIAZOLE AGONISTS OF THE APJ RECEPTOR
Compounds of Formula I and Formula II, pharmaceutically acceptable salt thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the following structures where the definitions of the variables are provided herein.
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Paragraph 0404

(2016/12/07)

TETRAHYDRONAPHTHALENE DERIVATIVES THAT INHIBIT MCL-1 PROTEIN
Provided herein are myeloid cell leukemia 1 protein (Mcl-1) inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula I, (I) and pharmaceutically acceptable salts thereof and pharmaceutical compositions containing the compounds. The compounds and compositions provided herein may be used, for example, in the treatment of diseases or conditions, such as cancer.
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Page/Page column 89; 90

(2016/03/22)

C70 as a Photocatalyst for Oxidation of Secondary Benzylamines to Imines
Photosensitive C70 was used for the catalytic oxidation of benzylamines to the corresponding imines. The advantages of using C70 compared to C60 or other commonly used photosensitizers such as tetraphenylporphyrin (TPP) ar
Kumar, Rakesh,Glei?ner, Eva H.,Tiu, Elisha Gabrielle V.,Yamakoshi, Yoko
supporting information
p. 184 - 187
(2016/02/05)

Compounds and pharmaceutical compositions thereof for the treatment of inflammatory disorders
The present invention discloses compounds according to Formula I: wherein Cy, R1, L1, R3, R4, R5, La, and Ra are as defined herein. Novel benzimidazoles according to Formula I, a
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Page/Page column 51

(2017/01/09)

Tandem catalysis of amines using porous graphene oxide
Porous graphene oxide can be used as a metal-free catalyst in the presence of air for oxidative coupling of primary amines. Herein, we explore a GO-catalyzed carbon-carbon or/and carbon-heteroatom bond formation strategy to functionalize primary amines in tandem to produce a series of valuable products, i.e., α-aminophosphonates, α-aminonitriles, and polycyclic heterocompounds. Furthermore, when decorated with nano-Pd, the Pd-coated porous graphene oxide can be used as a bifunctional catalyst for tandem oxidation and hydrogenation reactions in the N-alkylation of primary amines, achieving good to excellent yields under mild conditions.
Su, Chenliang,Tandiana, Rika,Balapanuru, Janardhan,Tang, Wei,Pareek, Kapil,Nai, Chang Tai,Hayashi, Tamio,Loh, Kian Ping
supporting information
p. 685 - 690
(2015/01/30)

Self-coupling of benzylamines over a highly active and selective supported copper catalyst to produce N-substituted amines by the borrowing hydrogen method
Amines were used as hydrogen donor for the borrowing hydrogen methodology with a heterogeneous catalyst. Supported copper catalysts catalyzed the self-condensation reaction of primary amines to secondary amines/imines with high efficiency. The recyclable, non-leaching catalyst is synthesized by a sol-gel method, which allows entrapping copper nanoparticles in an alumina matrix. The synthesized copper catalysts were found to be active in the self-coupling of primary amines to produce secondary amines. The hydrogen donor for the transfer hydrogenation appears to be the primary amine, and no additional hydrogen or hydrogen transfer reagent is required. To the best of our knowledge, this is the first report of a copper based catalyst for this type of reaction using the borrowing hydrogen scheme.
Liu, Huihui,Chuah, Gaik-Khuan,Jaenicke, Stephan
p. 262 - 268
(2015/06/23)

Synthesis and biological evaluation of pentanedioic acid derivatives as farnesyltransferase inhibitors
Structure-based virtual screening of a commercial library identified pentanedioic acid derivatives (6 and 13b) as a kind of novel scaffold farnesyltransferase inhibitors (FTIs). Chemical modifications of the lead compounds, biological assays and analysis of the structure-activity relationships (SAR) were conducted to discover more potent FTIs. Some of them displayed excellent inhibition against FTase, and among them, the most active compound 13n with an IC50 value of 0.0029 μM and SAR analysis might be helpful to the discovery of more potent FTIs. This journal is
Yang, Liuqing,Liu, Wei,Mei, Hanbing,Zhang, Yuan,Yu, Xiaojuan,Xu, Yufang,Li, Honglin,Huang, Jin,Zhao, Zhenjiang
supporting information
p. 671 - 676
(2015/04/27)

NOVEL COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF INFLAMMATORY DISORDERS
The present invention discloses compounds according to Formula I: wherein Cy, R1, L1, R3, R4, R5, La, and Ra are as defined herein. Novel benzimidazoles according to Formula I, a
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Paragraph 0419-0420

(2015/07/27)

BENZIMIDAZOLE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF INFLAMMATORY DISORDERS
The present invention discloses compounds according to Formula (I) wherein Cy, R1, L1 R3, R4, R5, La, and Ra are as defined herein. Novel benzimidazoles according to Formula (I),
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Paragraph 00237; 00312

(2015/08/06)

7-Azaindole-1-carboxamides as a new class of PARP-1 inhibitors
7-Azaindole-1-carboxamides were designed as a new class of PARP-1 inhibitors The compounds displayed a variable pattern of target inhibition profile that, in part, paralleled the antiproliferative activity in cell lines characterized by homologous recombination defects A selected compound (1l; ST7710AA1) showed significant in vitro target inhibition and capability to substantially bypass the multidrug resistance mediated by Pgp In antitumor activity studies against the MX1 human breast carcinoma growth in nude mice, the compound exhibited an effect similar to that of Olaparib in terms of tumor volume inhibition when used at a lower dose than the reference compound Treatment was well tolerated, as no deaths or significant weight losses were observed among the treated animals
Cincinelli, Raffaella,Musso, Loana,Merlini, Lucio,Giannini, Giuseppe,Vesci, Loredana,Milazzo, Ferdinando M.,Carenini, Nives,Perego, Paola,Penco, Sergio,Artali, Roberto,Zunino, Franco,Pisano, Claudio,Dallavalle, Sabrina
p. 1089 - 1103
(2014/02/14)

Three-component asymmetric catalytic ugi reaction - Concinnity from diversity by substrate-mediated catalyst assembly
The first chiral catalyst for the three-component Ugi reaction was identified as a result of a screen of a large set of different BOROX catalysts. The BOROX catalysts were assembled in situ from a chiral biaryl ligand, an amine, water, BH3×SMe2, and an alcohol or phenol. The catalyst screen included 13 different ligands, 12 amines, and 47 alcohols or phenols. The optimal catalyst system (LAP 8-5-47) provided α-amino amides from an aldehyde, a secondary amine, and an isonitrile with excellent asymmetric induction. The catalytically active species is proposed to be an ion pair that consists of the chiral boroxinate anion and an iminium cation. Harmonious arrangement of parts: A screen of BOROX catalysts that were generated in situ from 13 different ligands and 47 alcohols led to the identification of an effective combination for the catalytic asymmetric three-component Ugi reaction. Experimental results suggest that the catalyst is a chiral polyborate anion, which then forms an ion pair with the iminium cation that is generated from aldehyde and secondary amine.
Zhao, Wenjun,Huang, Li,Guan, Yong,Wulff, William D.
p. 3436 - 3441
(2014/04/03)

Pseudorotaxane orientational stereoisomerism driven by π-electron density
Pseudo[2]rotaxane orientational isomers were formed in a stereocontrolled way by exploiting the electron-withdrawing (EW) or electron-donating (ED) effects of para-substituted dibenzylammonium axles threaded through the π-electron rich calixarene cavity, which allow the fine tuning of the weak π-π interactions.
Gaeta, Carmine,Talotta, Carmen,Neri, Placido
supporting information
p. 9917 - 9920
(2014/08/18)