- Practical copper-catalyzed N-arylation of amines with 20% aqueous solution of n-Bu4NOH
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N-Arylation of a wide variety of amines with phenylboronic acid catalyzed by copper acetate under 20% aqueous solution of n-Bu4NOH was accomplished in good to excellent yields (up to 92%) and substrate conversions (up to 96%).
- Molaei, Hamidreza,Ghanbari, Mohammad Mehdi
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- Visible-Light-Mediated Chan-Lam Coupling Reactions of Aryl Boronic Acids and Aniline Derivatives
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The copper(II)-catalyzed aerobic oxidative coupling reaction between aryl boronic acids and aniline derivatives was found to be improved significantly under visible-light-mediated photoredox catalysis. The substrate scope of this oxidative Chan-Lam reaction was thus expanded to include electron-deficient aryl boronic acids as viable starting materials. Two are better than one: The copper(II)-catalyzed aerobic oxidative coupling reaction between aryl boronic acids and anilines is significantly improved by the addition of visible-light-mediated photoredox catalysts. The substrate scope of this Chan-Lam reaction was thus expanded to include electron-deficient aryl boronic acids.
- Yoo, Woo-Jin,Tsukamoto, Tatsuhiro,Kobayashi, Shu
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- Synthesis and characterization of new square planar heteroleptic cationic complexes [Ni(ii) β-oxodithioester-dppe]+; Their use as a catalyst for Chan-Lam coupling
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Novel heteroleptic [Ni(ii) β-oxodithioester-dppe]+PF6- complexes (β-oxodithioester = methyl-3-hydroxy-3-benzyl-2-propenedithioate L1 1, methyl-3-hydroxy-3-(p-methoxyphenyl)-2-propenedithioate L2 2, methyl-3-hydroxy-3-(naphthyl)-2-propenedithioate L3 3, methyl-3-hydroxy-3-(p-chlorophenyl)-2-propenedithioate L4 4, methyl-3-hydroxy-3-(p-bromophenyl)-2-propenedithioate L5 5 and methyl-3-hydroxy-3-(p-cyanophenyl)-2-propenedithioate L6 6) have been synthesized and characterized by elemental (C, H, N) analysis, ESI-MS, IR, UV-visible, 1H, 13C{1H}, 31P{1H} and 19F{1H} NMR spectroscopy. The distorted square planar structures of the isomorphous cationic complexes 2, 3, 4 and 5 have been determined by X-ray crystallography. The catalytic activities of 1-6 were investigated for the Chan-Lam coupling reaction involving arylboronic acids and amines to afford N-arylated products in good to excellent yields under mild conditions with 1 mol% catalyst loading. This catalytic protocol offers significant functional group tolerance, and is endowed with a broad substrate scope. This journal is
- Kumari, Kavita,Kumar, Saurabh,Singh, Krishna Nand,Drew, Michael G. B.,Singh, Nanhai
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- Imidazole-directed fabrication of three polyoxovanadate-based copper frameworks as efficient catalysts for constructing C-N bonds
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A synthetic pathway for the directed preparation of three novel polyoxovanadate-based copper frameworks (POVCFs), i.e., [Cu0.5(1-ipIM)2]2[V4O11] (POVCF 1), [Cu(1-ipIM)2](VO3)2 (POVCF 2) and [Cu(1-pIM)4](HpIM)4[V10O28] (POVCF 3) (1-ipIM = 1-isopropylimidazole; 1-pIM = 1-propylimidazole) using bifunctional imidazole molecules as organic ligands and base has been developed. Systematic studies revealed that the variable base enviroment in the reaction is the key step in the preparation of 1D to 3D supermolecular networks of POVCFs 1-3. Single crystal X-ray diffraction analyses demonstrated that the Cu2+ atoms of POVCFs 1-2 were coordinated with four imidazole derivative molecules and two different polyoxovanadate {[V4O11]2- and [V10O28]6-} clusters, respectively, exhibiting a [CuN4O2] binding set and a distorted octahedral geometry. Specifically, POVCF 1 exhibited adjacent [V4O11]2- that dangle up and down arranged in a parallel 2D network and further coordinated with [Cu(1-ipIM)4]2+ to form a 3D supramolecular structure. However, POVCF 3 presented one tetrahedral coordinated vanadium atom and one four-coordinated copper atom and they further gave rise to a 1D network by the Cu-O and V-O bonds. More importantly, these POVCFs were further studied in the construction of C-N bond reactions of primary amines under mild conditions, and it was found that POVCF 1 displayed efficient heterogeneous catalytic activities in the Chan-Lam reaction (yields up to 89%). This journal is
- Gong, Shuwen,Gu, Yuxiao,Huang, Xianqiang,Li, Jikun,Li, Qiang,Qi, Yuquan,Shen, Guodong
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- Electrochemically Enabled Chan-Lam Couplings of Aryl Boronic Acids and Anilines
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The Chan-Lam reaction remains a highly utilized transformation for C-N bond formation. However, anilines remain problematic substrates due to their lower nucleophilicity. To address this problem, we developed an electrochemically mediated Chan-Lam coupling of aryl boronic acids and amines utilizing a dual copper anode/cathode system. The mild conditions identified have enabled the preparation of a wide range of functionalized biarylanilines in good yields and chemoselectivities.
- Wexler, Ryan P.,Nuhant, Philippe,Senter, Timothy J.,Gale-Day, Zachary J.
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- Design, preparation and characterization of aerogel NiO-CuO-CoO/SiO2 nanocomposite as a reusable catalyst for C-N cross-coupling reaction
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Aerogels are porous, non-crystalline solid materials with high specific surface space, plentiful three-dimensional (3D) porous construction, ultra-low density and significant porosity. The aerogel nanocomposite is produced using sol-gel and supercritical drying processes. CO2 supercritical drying (SCD) is the most powerful process, ensuring optimal product properties such as high porosity, low density, and high thermal conductivity. On this account, we used the CO2 supercritical drying method to produce NiO-CuO-CoO/SiO2 nanocomposite aerogels and applied it as a reusable catalyst for the C-N cross-coupling reaction (Buchwald-Hartwig amination). Powerful catalytic activity for the C-N cross-coupling reaction was obtained for the new nanocomposite aerogel, that is, NiO-CuO-CoO/SiO2. The catalyst was characterized by X-ray Powder Diffraction (XRD), field emission scanning electron microscopy (FE-SEM), energy-dispersive X-ray spectroscopy (EDS), elemental mapping and Brunauer-Emmett-Teller (BET). Also, organic compounds were identified by melting point, Fourier-transform infrared spectroscopy (FT-IR) and hydrogen-1 nuclear magnetic resonance (1H NMR) analyses.
- Ghasemi, Amir Hossein,Naeimi, Hossein
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- N-arylation of amines with o-silylaryl triflate
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An efficient, transition-metal-free procedure for the N-arylation of amines 1 has been achieved by allowing those substrates to react with o-silylaryl triflate 2 in the presence of CsF. Good to excellent yields of arylated products 3 are obtained under very mild reaction conditions. This chemistry readily tolerates a variety of functional groups.
- Lee,Jung,Hahn
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- Metal-free synthesis of secondary amines by the reaction of tosyl triazene and aryl boronic acid
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A metal free noncatalytic amination process has been developed for the synthesis of N-substituted aniline using a new amine source. The amine source p-toluene sulfonyl triazene (PhN?NNHTs) has been prepared by treating aryldiazonium salt with p-tosylamide. Various unsymmetrical amines could be synthesized by treating this reagent and boronic acid in toluene at 110 °C in the presence of DBU and 4 ? molecular sieve. A large variety of N-substituted aniline could be synthesized with moderate yield.
- Sarma, Manas Jyoti,Phukan, Prodeep
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- Novel boron compounds and Organic light emitting diode including the same
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The present invention relates to a boron compound usable in an organic light-emitting device, and an organic light-emitting device comprising the same and, more particularly, to a boron compound represented by any one of chemical formula A to chemical formula D and an organic light-emitting device comprising the same. The chemical formula A to chemical formula D are the same as described in the detailed description of the invention. When the novel boron compound is used as a dopant material in an organic light-emitting device, the organic light-emitting device exhibits longer life characteristics compared to the prior art.
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Paragraph 0361; 0370-0373
(2021/02/02)
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- Visible-Light- And PPh3-Mediated Direct C-N Coupling of Nitroarenes and Boronic Acids at Ambient Temperature
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We present here a metal-free, visible-light- and triphenylphosphine-mediated intermolecular, reductive amination between nitroarenes and boronic acids at ambient temperature without any photocatalyst. Mechanistically, a slow reduction of nitroarenes to a nitroso and, finally, a nitrene intermediate occurs that leads to the amination product with concomitant 1,2-aryl/-alkyl migration from a boronate complex. A wide range of nitroarenes underwent C-N coupling with aryl-/alkylboronic acids providing high yields.
- Manna, Kartic,Ganguly, Tanusree,Baitalik, Sujoy,Jana, Ranjan
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supporting information
p. 8634 - 8639
(2021/11/01)
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- POLYCYCLIC AROMATIC DERIVATIVE COMPOUNDS AND ORGANIC LIGHT-EMITTING ELEMENTS USING THE SAME
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PROBLEM TO BE SOLVED: To provide: organic light-emitting compounds used in organic layers of organic light-emitting elements and capable of realizing efficient and long-lasting organic light-emitting elements; and organic light-emitting elements comprising the same. SOLUTION: An organic light-emitting compound is such that Q1 to Q3 are linked by linkers Y and X at specific positions, where Q1 to Q3 are identical to or different from each other and each independently a substituted or unsubstituted C6-50 aromatic hydrocarbon ring or a substituted or unsubstituted C2-50 heteroaromatic ring; each of the linkers Y is one selected from among N-R1, CR2R3, O, S, Se and SiR4R5; the multiple linkers Y are identical to or different from each other; and X is one selected from among B, P and P=O. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
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Paragraph 0108; 0117-0120
(2020/06/30)
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- POLYCYCLIC AROMATIC COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICES USING THE SAME
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Disclosed are polycyclic aromatic compounds that can be employed in various organic layers of organic electroluminescent devices. Also disclosed are organic electroluminescent devices including the polycyclic aromatic compounds. The organic electroluminescent devices are highly efficient and long lasting and have greatly improved luminous efficiency.
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Paragraph 0076-0078
(2020/06/29)
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- Chan-Evans-Lam C?N Coupling Promoted by a Dinuclear Positively Charged Cu(II) Complex. Catalytic Performance and Some Evidence for the Mechanism of CEL Reaction Obviating Cu(III)/Cu(I) Catalytic Cycle
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In the present study, we report the synthesis of a series of copper(II) complexes with a wide range of ligands and their testing in the copper catalyzed Chan-Evans-Lam (CEL) coupling of aniline and phenylboronic acid. The efficiency of the coupling was directly connected with the ease of the reduction of Cu(II) to Cu(I) of the complexes. The most efficient catalyst was derived from 4-t-butyl-2,5-bis[(quinolinylimino)methyl]phenolate and two Cu(II) ions. Depending on the counter-anion nature and the concentration of the reaction mixture, the reaction can be directed to predominant C?N-bond formation. Forty-three derivatives of diphenylamine were prepared under the optimized conditions. The proposed mechanism of the catalysis was based on the reduction potential of a series of complexes, molecular weight measurements of the catalytic complex in MeOH and the kinetic studies of aniline and phenylboronic acid coupling. In addition, an 1H NMR experiment in a sealed NMR tube, without external oxygen supply available, proved that no complete Cu(II) to Cu(I) conversion was observed under the condition, ruling out the usually accepted mechanism of the C?N coupling, which included the oxygenation of the intermediately formed Cu(I) complexes after the key step of C?N conversion had already been completed. Instead, a mechanism was proposed, involving an oxygen molecule coordinated to two copper ions in the key C?N bond formation without any detectable conversion of the Cu(II) complexes to Cu(I).
- Akatyev, Nikolay,Il'in, Mikhail,Il'in, Mikhail,Peregudova, Svetlana,Peregudov, Alexander,Buyanovskaya, Anastasiya,Kudryavtsev, Kirill,Dubovik, Alexander,Grinberg, Valerij,Orlov, Victor,Pavlov, Alexander,Novikov, Valentin,Volkov, Ilya,Belokon, Yuri
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p. 3010 - 3021
(2020/04/29)
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- PROSTACYCLIN RECEPTOR AGONIST
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A compound represented by formula (I) or an isomer or a pharmaceutically acceptable salt thereof. The present invention also relates to an application of the same in preparing a drug for treating a disease related to a PGI2 receptor.
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Paragraph 0088-0090; 0145-0147
(2020/12/22)
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- Reductive Molybdenum-Catalyzed Direct Amination of Boronic Acids with Nitro Compounds
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The synthesis of aromatic amines is of utmost importance in a wide range of chemical contexts. We report a direct amination of boronic acids with nitro compounds to yield (hetero)aryl amines. The novel combination of a dioxomolybdenum(VI) catalyst and triphenylphosphine as inexpensive reductant has revealed to be decisive to achieve this new C?N coupling. Our methodology has proven to be scalable, air and moisture tolerant, highly chemoselective and engages both aliphatic and aromatic nitro compounds. Moreover, this general and step-economical synthesis of aromatic secondary amines showcases orthogonality to other aromatic amine syntheses as it tolerates aryl halides and carbonyl compounds.
- Suárez-Pantiga, Samuel,Hernández-Ruiz, Raquel,Virumbrales, Cintia,Pedrosa, María R.,Sanz, Roberto
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supporting information
p. 2129 - 2133
(2019/01/25)
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- Copper-catalyzed, ceric ammonium nitrate mediated N-arylation of amines
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Cu-Catalyzed, ligand- and base-free cross-coupling of aryl boronic acids with primary and secondary amines has been reported. This ‘Chan-Evans-Lam' reaction has revealed that at room temperature, with a catalytic amount of copper(ii) acetate and ceric ammonium nitrate (CAN) as an oxidant, N-arylation can result in an effective C-N bond formation. This air stable, practical, robust protocol enables tolerance towards a variety of functional groups on both boronic acid and amine partners.
- Gonela, Uma Maheshwar,Ablordeppey, Seth Y.
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supporting information
p. 2861 - 2864
(2019/02/17)
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- Copper immobilized at a covalent organic framework: An efficient and recyclable heterogeneous catalyst for the Chan-Lam coupling reaction of aryl boronic acids and amines
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A polyimide covalent organic framework (PI-COF) with high thermal and chemical stabilities has been readily prepared from commercially available and inexpensive reagents and was employed as an effective support for heterogeneous copper. It was demonstrated that the obtained Cu@PI-COF is a highly active heterogeneous catalyst which can effectively promote the Chan-Lam coupling reaction of aryl boronic acids and amines in an open flask without the aid of any base or additive. In addition, the catalyst could be readily recovered from the reaction mixture by simple filtration and reused for at least eight cycles without any observable change in structure and catalytic activity.
- Han, Yi,Zhang, Mo,Zhang, Ya-Qing,Zhang, Zhan-Hui
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p. 4891 - 4900
(2018/11/21)
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- Structures and phase transition of three isomers of 1-phenylindolin-2-one derivatives: 6-chloro-1-phenylindolin-2-one, 4-chloro-1-phenylindolin-2-one and 1-(3-chlorophenyl)indolin-2-one
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Three 1-phenylindolin-2-one derivatives, namely 6-chloro-1-phenylindolin-2-one (A), 4-chloro-1-phenylindolin-2-one (B) and 1-(3-chlorophenyl)indolin-2-one (C), all C14H10ClNO, have been synthesized and the structures of these compounds at room temperature (ART, BRT and CRT) and low temperature (ALT, BLT and CLT) have been determined. Crystal A at 295 K (ART) crystallized in the monoclinic space group P21/c and the phenyl ring of the unique molecule exhibits disorder over two positions. At low temperature, the disorder disappeared and crystal A at 90 K (ALT) crystallized in the triclinic space group P with a doubled unit-cell volume and four molecules in the asymmetric unit. Density functional theory (DFT) calculations revealed a low oscillation barrier (0.24 kcal mol?1) of the phenyl ring of molecule A and the phase transition from the P21/c structure to the P structure can be interpreted in terms of the freezing out of the two conformations at low temperature. Crystal B retains space group P21/c in the temperature range from 100 to 297 K. A kind of obtuse-cell to acute-cell change can be recognized; if the unit cell of BLT at 100 K is set to be a standard obtuse cell [β = 90.341 (2)°] and the cell is kept untransformed in the course of temperature changing, the cell of BRT at 297 K was found to be acute [β = 89.288 (2)°]. The molecules in structure C are packed in layers, with C—H…O hydrogen bonds between neighbouring layers.
- Wang, Bing,Fang, Qi
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p. 1750 - 1758
(2018/12/13)
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- Palladium- and Nickel-Catalyzed Amination of Aryl Fluorosulfonates
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Examples of the palladium- and nickel-catalyzed amination of aryl fluorosulfonates with aromatic and alkyl amines are described. Aniline is coupled to a diverse series of aryl fluorosulfonates catalyzed by the combination of CpPd(cinammyl) and Xantphos, and the relative reactivity of aryl fluorosulfonates to undergo Pd-catalyzed amination was compared with other common aryl electrophiles. In addition, we report the direct amination of a phenol by in situ formation of an aryl fluorosulfonate by reaction with sulfuryl fluoride and base followed by subsequent amination to form a new C-N bond. Finally, we report examples of the nickel-catalyzed amination of aryl fluorosulfonates catalyzed by the combination of Ni(COD)2 and DPPF in the presence of MeCN. The high reactivity of the aryl fluorosulfonate electrophile with generic palladium and nickel catalyst systems, combined with its simple preparation from sulfuryl fluoride will enable commercial amination reactions of abundant phenolic raw materials.
- Hanley, Patrick S.,Clark, Thomas P.,Krasovskiy, Arkady L.,Ober, Matthias S.,O'Brien, John P.,Staton, Tina S.
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p. 3515 - 3519
(2016/07/06)
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- A method for preparing aromatic amine derivative
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The invention discloses a preparation method of a diarylamine ramification. The preparation method comprises the following steps: dissolving a phenylamine ramification, a phenylhydrazine ramification, a metal phthalocyanine ramification and a copper salt into a solvent, and reacting at -10 to 40 DEG C to obtain the diarylamine ramification. According to the preparation method, the phenylamine ramification and the phenylhydrazine ramification are taken as starting materials, so that raw materials are easy to obtain and plenty in variety; a product obtained by utilizing the method is plenty in type, can not only be directly used, but also be used for other further reactions; and no additive is required to be added. The preparation method disclosed by the invention has the advantages of short synthetic route, moderation in reaction condition, simple reaction operation and post-processing process, high yield and suitability for large-scale production.
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Paragraph 0126-0129
(2016/10/08)
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- CoPc/Cu(OAc)2-catalyzed N-arylation of amines with arylhydrazines leading to N-aryl amines
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The N-arylation of amines with arylhydrazines has been developed, achieving the selective cross-coupling of aryl radicals with amines to form N-aryl amines. The reaction uses air as an oxidant, CoPc and Cu(OAc)2as catalysts. The reaction proceeds under mild conditions in air through a relay process, arylhydrazines are oxidized to aryldiazenes by CoPc, further oxidized to aryl radicals by air (O2), which are trapped by Cu(OAc)2–amine complex, followed by reduction–elimination reaction to form N-aryl amines. Arylamines and arylhydrazines give the highest yields, but N-aryl-N-alkylamines and N-alkylamines can be used as well.
- Sun, Wang-Bin,Zhang, Pei-Zhi,Jiang, Tao,Li, Cheng-Kun,An, Li-Tao,Shoberu, Adedamola,Zou, Jian-Ping
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p. 6477 - 6483
(2016/09/23)
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- METHOD FOR COUPLING A FLUOROSULFONATE COMPOUND WITH AN AMINE COMPOUND
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The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an amine; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound. The present disclosure further describes a one-pot method for coupling a first compound to a second compound.
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Paragraph 0050-0051
(2016/05/02)
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- N-(Pyridin-2-yl)benzamide: Efficient ligand for the nickel catalyzed Chan-Lam cross-coupling reaction
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An efficient protocol for the Chan-Lam cross-coupling reactions of arylboronic acids with aryl or alkyl amines has been developed by employing simple N-(pyridin-2-yl)benzamide ligand with Ni(OAc)2·4H2O in the presence of TMG base. The reaction proceeded well with high yields by employing various N-nucleophiles at low catalytic loadings.
- Keesara, Srinivas
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p. 6685 - 6688
(2016/01/28)
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- Tricyclic phenothiazine and phenoselenazine derivatives as potential multi-targeting agents to treat Alzheimer's disease
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A group of tricyclic phenothiazines (6a, 6b and 7a-l) and phenoselenazines (12a, 12b and 13a-l) was designed, synthesized and evaluated as multi-targeting ligands aimed at the cholinergic, amyloid and oxidative stress pathways of Alzheimer's disease. The phenothiazine derivative 7j (2-chloro-10H-phenothiazin-10-yl-(4-methoxyphenyl)methanone) was identified as the best dual, non-selective cholinesterase inhibitor (AChE IC50 = 5.9 ± 0.6 μM; BuChE IC50 = 5.3 ± 0.5 μM), whereas in the corresponding phenoselenazine series, 13j (2-chloro-10H-phenoselenazin-10-yl-(4-methoxyphenyl)methanone) exhibited good non-selective cholinesterase inhibition (AChE IC50 = 5.8 ± 0.4 μM; BuChE IC50 = 4.9 ± 0.5 μM). Interestingly, N-10 unsubstituted phenothiazine 6a (AChE IC50 = 7.3 ± 0.6 μM; BuChE IC50 = 5.8 ± 0.5 μM; Aβ1-42 aggregation inhibition = 62%; DPPH scavenging = 92%), and the corresponding phenoselenazine bioisostere 12a (AChE IC50 = 5.6 ± 0.4 μM; BuChE IC50 = 3.0 ± 0.5 μM; Aβ1-42 aggregation inhibition = 45.6%; DPPH scavenging = 84.4%) were able to exhibit multi-targeting ability by demonstrating cholinesterase inhibition, beta-amyloid aggregation and antioxidant properties. These results show that fused tricyclic ring systems based on either phenothiazine or phenoselenazine templates can be useful to develop hybrid small molecules to target multiple pathological routes associated with Alzheimer's disease.
- Tin, Gary,Mohamed, Tarek,Gondora, Nyasha,Beazely, Michael A.,Rao, Praveen P. N.
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p. 1930 - 1941
(2015/11/17)
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- Aerobic synthesis of biocompatible copper nanoparticles: Promising antibacterial agent and catalyst for nitroaromatic reduction and C-N cross coupling reaction
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Herein, we report the synthesis of copper nanoparticles at ambient conditions using biopolymer, pectin, as a protecting agent and hydrazine as a reducing agent. The obtained nanoparticles catalyze the reduction of nitroaromatic compounds in aqueous solution and also catalyze the C-N cross coupling of amines with bromobenzene in good yields. This journal is the Partner Organisations 2014.
- Venkatakrishnan, Showmya,Veerappan, Ganapathy,Elamparuthi, Elangovan,Veerappan, Anbazhagan
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p. 15003 - 15006
(2014/04/17)
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- Triphenyltin chloride as a new source of phenyl group for C-heteroatom and C-C bond formation
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Ph3SnCl is introduced as a very suitable source of phenyl group for coupling with phenols, amines, and thiols in the presence of Cu(OAc)2 in Et3N at room temperature to give aryl ethers, amines, and arylthio ethers in high yields. In addition, the application of Ph3SnCl in the Stille coupling of aryl halides in the presence of Pd(0) catalyst in PEG 400 at 110C is discussed.
- Iranpoor, Nasser,Firouzabadi, Habib,Elham, Etemadi Davan,Rostami, Abed,Nematollahi, Arash
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p. 123 - 130
(2013/10/01)
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- Direct amination of phenols under metal-free conditions
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Herein, we disclose the metal-free synthesis of arylamines via the direct amination of phenols using aminating reagents. This reaction procedure uses easy accessible aminating reagents and provides a versatile synthetic route to a broad range of arylamines with various functionalities in good to excellent yield. By using a two-step route of amination and oxidative coupling reaction, we synthesized three naturally occurring carbazole alkaloids: murrayafoline A, mukonine, and clausenine from two commercially available phenols. Georg Thieme Verlag Stuttgart · New York.
- Yu, Jianzhong,Wang, Yongtao,Zhang, Peizhi,Wu, Jun
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supporting information
p. 1448 - 1454
(2013/07/26)
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- Metal-free synthesis of secondary arylamines: An aliphatic-to-aromatic transformation
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An efficient method for the N-arylation of primary and some secondary amines using 2-halocyclohex-2-enones in an aliphatic-to-aromatic transformation in the presence of a substoichiometric amount of pTsOH has been developed. A series of arylamines have been synthesized from 2-halocyclohex-2-enones by in situ enamine formation followed by aromatization under environmentally friendly conditions using pTsOH. This metal-free, practical, relatively inexpensive protocol is of value in organic synthesis for industrial and academic applications. Copyright
- Barros, M. Teresa,Dey, Suvendu S.,Maycock, Christopher D.
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supporting information
p. 742 - 747
(2013/03/13)
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- Heteroaromatic-aminomethyl quinolones: Potent and selective iNOS inhibitors
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The overproduction of nitric oxide during the biological response to inflammation by the nitric oxide synthase (NOS) enzymes have been implicated in the pathology of many diseases. By removal of the amide core from uHTS-derived quinolone 4, a new series highly potent heteroaromatic-aminomethyl quinolone iNOS inhibitors 8 were identified. SAR studies led to identification of piperazine 22 and pyrimidine 32, both of which reduced plasma nitrates following oral dosing in a mouse lipopolysaccharide challenge assay.
- Duron, Sergio G.,Lindstrom, Andrew,Bonnefous, Celine,Zhang, Hui,Chen, Xiaohong,Symons, Kent T.,Sablad, Marciano,Rozenkrants, Natasha,Zhang, Yan,Wang, Li,Yazdani, Nahid,Shiau, Andrew K.,Noble, Stewart A.,Rix, Peter,Rao, Tadimeti S.,Hassig, Christian A.,Smith, Nicholas D.
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scheme or table
p. 1237 - 1241
(2012/03/11)
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- Anionic N-fries rearrangement of N-carbamoyl diarylamines to anthranilamides. Methodology and application to acridone and pyranoacridone alkaloids
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A general alkyllithium/LDA-mediated rearrangement of N-carbamoyl diarylamines 7a-g into the anthranilamides 8a-g and 9a-g (Table 1) is presented and applied to a regioselective efficient construction of acridone (17) and pyranoacridone (18) alkaloids (Scheme 4).
- MacNeil, Stephen L.,Wilson, Brian J.,Snieckus, Victor
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p. 1133 - 1136
(2007/10/03)
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- Diphenylamino and indolyl substituted pyromellitides
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This invention relates to 3,7-bis(disubstituted aminophenyl- or indolyl)-3,7-bis(diphenylamino)pyromellitides, 3,5-bis(disubstituted aminophenyl- or indolyl)-3,5-bis(diphenylamino)pyromellitides and mixtures thereof useful as color formers, particularly in carbonless duplicating and thermal marking systems, which are prepared by the interaction of 2,5-bis(disubstituted aminophenyl- or indolyl)carbonyl-1,4-benzenedicarboxylic acids or 2,4-bis(disubstituted aminophenyl- or indolyl)carbonyl-1,5-benzenedicarboxylic acids and mixtures thereof with diphenylamines.
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- DISSOCIATION CONSTANTS OF MONOSUBSTITUTED DIPHENYLAMINES AND AN OPTIMIZED CONSTRUCTION OF ACIDITY FUNCTION
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Eleven monosubstituted diphenylamines have been synthesized, and concentration ratio of the protonated and free bases has been measured in aqueous sulphuric acid in the concentration range 1.0*10-3 to 9.0 mol l-1.An algorithm has been suggested and used for determination of optimized values of pK and H" acidity function within sulphuric acid concentration range 0.05 to 9.0 mol l-1.The results have been compared with literature data and discussed in terms of theory of acidity functions and linear free energy relationships.
- Pytela, Oldrich,Vetesnik, Pavel
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p. 2368 - 2375
(2007/10/02)
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- MONO(m-SUBSTITUTED) CHLOROACETYLDIARYLAMINES IN THE STOLLE REACTION
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The effect of substituted (OCH3, Cl) on the ratio of the isomeric N-aryloxindoles formed in the Stolle reaction from mono(m-substituted) chloroacetyldiarylamines was studied.It was shown by means of gas-liquid chromatography (GLC) and PMR spectroscopy that in the case of the methoxy group electrophilic substitution occurs only in the ring activated by the substituent.The presence of a halogen atom leads only to 1-(m-chlorophenyl)oxindole.The results show that high selectivity of the attack by the carbonium ion on the phenyl rings with electron-donor and electron-acceptor substituents is also retained in the case of intramolecular electrophilic substitution under conditions of kinetic control.
- Przheval'skii, N. M.,Grandberg, I. I.
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p. 716 - 719
(2007/10/02)
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- Micellar Catalysis of the Basic Hydrolysis of Amides. 4. Substituted N,N-Diphenylbenzamides
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The cytalysis of the basic hydrolysis of a series of N-aryl-N-phenylbenzamides (1) and a series of substituted N,N-diphenylbenzamides (2) by micelles of cetyltrimethylammonium bromide (ctab) has been studied.On the basis of the effects of substituents on the aromatic ring attached to the nitrogen atom, a mechanistic change on transfer from water to a micellar environment is proposed.In water the mechanism involves rate-determining solvent-assisted carbon-nitrogen bond breaking (mechanism B), while in the presence of micelles of ctab, a rate-determining attack of hydroxide ion (mechanism C) is proposed.Reasons for mechanistic change are discussed.
- Broxton, Trevor J.,Fernando, Denise R.,Rowe, Jeffrey E.
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p. 3522 - 3525
(2007/10/02)
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