- Hydrosilylation and Mukaiyama aldol-type reaction of quinolines and hydrosilylation of imines catalyzed by a mesoionic carbene-stabilized borenium ion
-
Aldimines and ketimines containing electron-donating and electron-withdrawing groups can be hydrosilylated with borenium catalysts at as low as 1 mol% catalyst loading at room temperature, providing the corresponding secondary amines in excellent yields. Reactions with 2-phenylquinoline gave the 1,4-hydrosilylquinoline product selectively which can be further functionalized in a one-pot synthesis to give unique γ-amino alcohol derivatives. Control experiments suggest that the borenium ion catalyzes both the hydrosilylation and subsequent addition to the aldehyde.
- Bestvater, Brian P.,Clarke, Joshua J.,Crudden, Cathleen M.,DeJesus, Joseph F.,Devaraj, Karthik,Eisenberger, Patrick,Kojima, Ryoto
-
supporting information
p. 6786 - 6791
(2021/08/20)
-
- Synthesis ofN-aryl amines enabled by photocatalytic dehydrogenation
-
Catalytic dehydrogenation (CD)viavisible-light photoredox catalysis provides an efficient route for the synthesis of aromatic compounds. However, access toN-aryl amines, which are widely utilized synthetic moieties,viavisible-light-induced CD remains a significant challenge, because of the difficulty in controlling the reactivity of amines under photocatalytic conditions. Here, the visible-light-induced photocatalytic synthesis ofN-aryl amines was achieved by the CD of allylic amines. The unusual strategy using C6F5I as an hydrogen-atom acceptor enables the mild and controlled CD of amines bearing various functional groups and activated C-H bonds, suppressing side-reaction of the reactiveN-aryl amine products. Thorough mechanistic studies suggest the involvement of single-electron and hydrogen-atom transfers in a well-defined order to provide a synergistic effect in the control of the reactivity. Notably, the back-electron transfer process prevents the desired product from further reacting under oxidative conditions.
- Kim, Jungwon,Kim, Siin,Choi, Geunho,Lee, Geun Seok,Kim, Donghyeok,Choi, Jungkweon,Ihee, Hyotcherl,Hong, Soon Hyeok
-
p. 1915 - 1923
(2021/02/22)
-
- Discovery of M3Antagonist-PDE4 Inhibitor Dual Pharmacology Molecules for the Treatment of Chronic Obstructive Pulmonary Disease
-
In this paper, we report the discovery of dual M3 antagonist-PDE4 inhibitor (MAPI) compounds for the inhaled treatment of pulmonary diseases. The identification of dual compounds was enabled by the intuition that the fusion of a PDE4 scaffold derived from our CHF-6001 series with a muscarinic scaffold through a common linking ring could generate compounds active versus both the transmembrane M3 receptor and the intracellular PDE4 enzyme. Two chemical series characterized by two different muscarinic scaffolds were investigated. SAR optimization was aimed at obtaining M3 nanomolar affinity coupled with nanomolar PDE4 inhibition, which translated into anti-bronchospastic efficacy ex vivo (inhibition of rat trachea contraction) and into anti-inflammatory efficacy in vitro (inhibition of TNFα release). Among the best compounds, compound 92a achieved the goal of demonstrating in vivo efficacy and duration of action in both the bronchoconstriction and inflammation assays in rat after intratracheal administration.
- Armani, Elisabetta,Rizzi, Andrea,Capaldi, Carmelida,De Fanti, Renato,Delcanale, Maurizio,Villetti, Gino,Marchini, Gessica,Pisano, Anna Rita,Pitozzi, Vanessa,Pittelli, Maria Gloria,Trevisani, Marcello,Salvadori, Michela,Cenacchi, Valentina,Puccini, Paola,Amadei, Francesco,Pappani, Alice,Civelli, Maurizio,Patacchini, Riccardo,Baker-Glenn, Charles A.G.,Van De Po?l, Hervé,Blackaby, Wesley P.,Nash, Kevin,Amari, Gabriele
-
supporting information
p. 9100 - 9119
(2021/07/19)
-
- BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant
-
A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.
- Fan, Qing-Hua,Liu, Xintong,Luo, Zhenli,Pan, Yixiao,Xu, Lijin,Yang, Ji,Yao, Zhen,Zhang, Xin
-
supporting information
p. 5205 - 5211
(2021/07/29)
-
- Quantitative NaH catalytic hydroboration of aldimines
-
The catalytic hydroboration of aldimines was demonstrated, with only 3 mol% NaH required for the quantitative production of secondary amines under minimal solvent conditions. In addition, chemoselective hydroboration in the presence of other reducible functional groups was achieved. DFT calculations were then used to propose a reaction mechanism for imine hydroboration. This journal is
- An, Duk Keun,Hwang, Hyonseok,Kim, Hanbi,Lee, Ji Hye
-
p. 11330 - 11335
(2020/07/15)
-
- In water alkylation of amines with alcohols through a borrowing hydrogen process catalysed by ruthenium nanoparticles
-
A simple and environmentally benign procedure for the synthesis of secondary amines in water has been developed. Combining Ru3(CO)12, tetraphenylcyclopentadienone and a small quantity of TGPS-750-M surfactant, primary and secondary alcohols were alkylated at N employing equimolar amounts of aromatic amines in water. The reaction occurs under microwave (MW) dielectric heating with high conversion and high yield. When required, the use of biomass-derived 2-MeTHF or GVL as a co-solvent is possible. Under the influence of MWs, a Ru nanoparticle-nanomicelle combination was formed acting as an effective and recyclable catalyst. This protocol was also employed for "in water" cyclisation to synthesise biologically relevant pyrrolobenzodiazepines (PBDs).
- Risi, Caterina,Calamante, Massimo,Cini, Elena,Faltoni, Valentina,Petricci, Elena,Rosati, Filippo,Taddei, Maurizio
-
supporting information
p. 327 - 331
(2020/02/13)
-
- 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)
-
- MOF-derived Ni?NC catalyst: Synthesis, characterization, and application in one-pot hydrogenation and reductive amination
-
MOF-derived catalysts with nickel nanoparticles (NPs) uniformly embedded in nitrogen doped carbon shells were developed by pyrolysis of nickel-based metal-organic frameworks (MOFs), in which amino groups were introduced to act as the nitrogen source and possible anchoring sites for Ni NPs. The resulting materials were characterized systematically. In the architecture of the catalysts, a core-shell structure was discovered, in which Ni NPs with a diameter of 6-7 nm were surrounded by N doped graphitic layers, indicating that the introduction of amino groups into precursors is beneficial to the dispersion of NPs. One-step hydrogenation and reductive amination (OHRA) is a promising route to produce secondary amines, which avoids tedious separation of intermediates. Accordingly, we applied the prepared composites as catalysts to OHRA of benzaldehyde with nitrobenzene. Among them, the catalyst pyrolyzed at 600 °C for 1.5 h exhibited the best catalytic performance (conversion: >99%, selectivity for N-benzylaniline: 97.96%) and excellent recyclability. N-doping remarkably promotes the dispersion and stability of Ni NPs, thus improving their catalytic activity and selectivity. Furthermore, the Ni-N species as well as synergism of Ni NPs and adjacent pyridinic N may also facilitate the activation of H2. And its excellent stability and recyclability can be attributed to the core-shell structure. The achieved success in MOF-derived nanocomposites may pave the way for further industrial applications.
- Li, Jiayi,Wang, Bowei,Qin, Yutian,Tao, Qin,Chen, Ligong
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p. 3726 - 3734
(2019/07/22)
-
- Unsymmetrical triazolyl-naphthyridinyl-pyridine bridged highly active copper complexes supported on reduced graphene oxide and their application in water
-
A novel unsymmetrical triazolyl-naphthyridinyl-pyridine ligand was designed and synthesized, and employed in the synthesis of a heterogeneous copper complex on reduced graphene oxide. The resulting copper composite was characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and energy dispersive X-ray spectroscopy (EDX). This supported copper catalyst containing unsymmetrical triazolyl-naphthyridinyl-pyridine (only 0.1 mol%) showed excellent catalytic activity in water with good recyclability. Various functionalized quinoline derivatives were successfully synthesized in high yields through the green strategy in water. Other heterocyclic compounds, such as pyridine, 2-(pyridin-2-yl)quinoline, 1,8-naphthyridine, 5,6-dihydronaphtho[1,2-b][1,8]naphthyridine and 2-(pyridin-2-yl)-1,8-naphthyridine derivatives, were achieved in water with more than 80% yields. Mechanism studies revealed that this transformation occurs via dehydrogenation, condensation, and transfer hydrogenation and dehydrogenation processes which was supported by a deuterium labeling experiment.
- Hu, Wenkang,Zhang, Yilin,Zhu, Haiyan,Ye, Dongdong,Wang, Dawei
-
supporting information
p. 5345 - 5351
(2019/10/11)
-
- Cobalt(II) Coordination Polymer as a Precatalyst for Selective Hydroboration of Aldehydes, Ketones, and Imines
-
Highly effective hydroboration precatalyst is developed based on a cobalt(II)-terpyridine coordination polymer (CP). The hydroboration of ketones, aldehydes, and imines with pinacolborane (HBpin) has been achieved using the recyclable CP catalyst in the presence of an air-stable activator. A wide range of substrates containing polar C=O or C=N bonds have been hydroborated selectively in excellent yields under ambient conditions.
- Wu, Jing,Zeng, Haisu,Cheng, Jessica,Zheng, Shengping,Golen, James A.,Manke, David R.,Zhang, Guoqi
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p. 9442 - 9448
(2018/07/05)
-
- Development of novel β-carboline-based hydroxamate derivatives as HDAC inhibitors with antiproliferative and antimetastatic activities in human cancer cells
-
A series of novel β-carboline-based hydroxamate derivatives 12a-k were designed and synthesized, and their biological activities in a series of in vitro assays were evaluated. Several of these β-carboline derivatives not only showed excellent HDAC1/3/6 inhibitory effects, but also displayed significant antitumor activities against five human cancer cells. The most potent compound 12f demonstrated the highest anticancer potency against cancer cell lines with IC50 values of 0.53–1.56 μM, which was considerably more potent than harmine (IC50 = 46.7–55.3 μM) and also three-to ten-fold lower than that of SAHA (IC50 = 4.48–6.26 μM). Immunoblot analysis revealed that 12f dose-dependently inhibited histone H3 and α-tubulin acetylation, confirming its HDAC inhibitory effects. Moreover, 12f significantly arrested HepG2 cells at G2/M phase through inhibiting cell cycle related protein CDK1 and cyclin B in a concentration dependent manner. Interestingly, 12f also exerted strong anti-metastasis activity by simultaneously reducing the protein level of MMP2 and MMP9 and inhibiting MAPK signaling pathway.
- Ling, Yong,Guo, Jing,Yang, Qiuxing,Zhu, Peng,Miao, Jiefei,Gao, Weijie,Peng, Yanfu,Yang, Jiaying,Xu, Kun,Xiong, Biao,Liu, Gongqing,Tao, Jinhua,Luo, Lin,Zhu, Qing,Zhang, Yanan
-
p. 398 - 409
(2018/01/01)
-
- Main-Group-Catalyzed Reductive Alkylation of Multiply Substituted Amines with Aldehydes Using H2
-
Given the growing demand for green and sustainable chemical processes, the catalytic reductive alkylation of amines with main-group catalysts of low toxicity and molecular hydrogen as the reductant would be an ideal method to functionalize amines. However, such a process remains challenging. Herein, a novel reductive alkylation system using H2 is presented, which proceeds via a tandem reaction that involves the B(2,6-Cl2C6H3)(p-HC6F4)2-catalyzed formation of an imine and the subsequent hydrogenation of this imine catalyzed by a frustrated Lewis pair (FLP). This reductive alkylation reaction generates H2O as the sole byproduct and directly functionalizes amines that bear a remarkably wide range of substituents including carboxyl, hydroxyl, additional amino, primary amide, and primary sulfonamide groups. The synthesis of isoindolinones and aminophthalic anhydrides has also been achieved by a one-pot process that consists of a combination of the present reductive alkylation with an intramolecular amidation and intramolecular dehydration reactions, respectively. The reaction showed a zeroth-order and a first-order dependence on the concentration of an imine intermediate and B(2,6-Cl2C6H3)(p-HC6F4)2, respectively. In addition, the reaction progress was significantly affected by the concentration of H2. These results suggest a possible mechanism in which the heterolysis of H2 is facilitated by the FLP comprising THF and B(2,6-Cl2C6H3)(p-HC6F4)2.
- Hoshimoto, Yoichi,Kinoshita, Takuya,Hazra, Sunit,Ohashi, Masato,Ogoshi, Sensuke
-
supporting information
p. 7292 - 7300
(2018/06/01)
-
- 1,3,4-OXADIAZOLE AMIDE DERIVATIVE COMPOUND AS HISTONE DEACETYLASE 6 INHIBITOR, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME
-
The present invention relates to novel compounds having histone deacetylase 6 (HDAC6) inhibitory activity, stereoisomers thereof or pharmaceutically acceptable salts thereof, the use thereof for the preparation of therapeutic medicaments, pharmaceutical compositions containing the same, a method for treating diseases using the composition, and methods for preparing the novel compounds. The novel compounds, stereoisomers thereof or pharmaceutically acceptable salts thereof according to the present invention have histone deacetylase 6 (HDAC6) inhibitory activity and are effective for the prevention or treatment of HDAC6-mediated diseases, including infectious diseases; neoplasms; endocrine, nutritional and metabolic diseases; mental and behavioral disorders; neurological diseases; diseases of the eye and adnexa; cardiovascular diseases; respiratory diseases; digestive diseases; diseases of the skin and subcutaneous tissue; diseases of the musculoskeletal system and connective tissue; or congenital malformations, deformations and chromosomal abnormalities.
- -
-
Paragraph 0054; 0055; 0056
(2018/06/15)
-
- Phosphorous(v) Lewis acids: Water/base tolerant P3-trimethylated trications
-
The water/base intolerance of the previously reported electrophilic phosphonium cations has been overcome by replacing the labile electron-withdrawing groups generally attached to phosphorus (e.g. -F, -OAr, -CF3) with methyl groups. Tri-phosphorus(v) tricationic species, accessible in one-pot from commercially available materials, are air and water/base tolerant, yet are sufficiently Lewis acidic for catalysis.
- Bayne,Fasano,Szkop,Ingleson,Stephan
-
supporting information
p. 12467 - 12470
(2018/11/20)
-
- BINAP-copper supported by hydrotalcite as an efficient catalyst for the borrowing hydrogen reaction and dehydrogenation cyclization under water or solvent-free conditions
-
A BINAP-Cu system supported by hydrotalcite has been developed and proved to be a highly efficient catalyst for the atom-efficient and green borrowing hydrogen reaction and dehydrogenative cyclization. This BINAP-Cu complex supported by hydrotalcite is highly air-stable and can be recycled at least five times under solvent-free conditions. Notably, 1-benzyl-2-aryl-1H-benzo[d]imidazole derivatives could be synthesized from alcohols in only one step with water as the solvent for the first time. This provided a much greener and efficient catalytic method towards the synthesis of functionalized amines, ketones and 1-benzyl-2-aryl-1H-benzo[d]imidazole derivatives with high yields under water or solvent-free conditions.
- Xu, Zhaojun,Yu, Xiaoli,Sang, Xinxin,Wang, Dawei
-
supporting information
p. 2571 - 2577
(2018/06/11)
-
- One-pot reductive amination of carbonyl compounds with nitro compounds with CO/H2O as the hydrogen donor over non-noble cobalt catalyst
-
The one-pot reductive amination of carbonyl compounds with nitro compounds over heterogeneous non-noble metal catalysts was developed for the first time by transfer hydrogenation with CO/H2O as the hydrogen donor. Nitrogen-doped carbon supported cobalt nanoparticles were observed to be active toward this reaction, affording structurally-diverse secondary amines with high yields. Kinetic studies revealed that the transfer hydrogenation of imines (C[dbnd]N bonds) was the rate-determining step. Reaction mechanism studies indicated that both nitrogen and cobalt nanoparticles were important for the transfer hydrogenation with CO/H2O to generate the proton (N[sbnd]H+) and hydride (Co[sbnd]H?) as the active species. Furthermore, the heterogeneous cobalt catalyst was highly stable without the loss of its catalytic activity during the recycling experiments.
- Zhou, Peng,Yu, Changlin,Jiang, Liang,Lv, Kangle,Zhang, Zehui
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p. 264 - 273
(2017/06/23)
-
- 1,3,4-OXADIAZOLE DERIVATIVE COMPOUNDS AS HISTONE DEACETYLASE 6 INHIBITOR, AND THE PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
-
The present invention relates to novel compounds having histone deacetylase 6 (HDAC6) in-hibitory activity, stereoisomers thereof or pharmaceutically acceptable salts thereof, the use thereof for the preparation of therapeutic medicaments, pharmaceutical compositions containing the same, a method for treating diseases using the composition, and methods for preparing the novel compounds. The novel compounds, stereoisomers thereof or pharmaceutically acceptable salts thereof according to the present invention have histone deacetylase (HDAC) inhibitory activity and are effective for the prevention or treatment of HDAC6-mediated diseases, including infectious diseases; neoplasms; endocrine, nutritional and metabolic diseases; mental and be-havioral disorders; neurological diseases; diseases of the eye and adnexa; cardiovascular diseases; respiratory diseases; digestive diseases; diseases of the skin and subcutaneous tissue; diseases of the musculoskeletal system and connective tissue; or congenital malformations, de? formations and chromosomal abnormalities.
- -
-
Paragraph 417-419
(2017/02/28)
-
- 1,3,4-OXADIAZOLE SULFAMIDE DERIVATIVE COMPOUNDS AS HISTONE DEACETYLASE 6 INHIBITOR, AND THE PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
-
The present invention relates to novel compounds having histone deacetylase 6 (HDAC6) inhibitory activity, stereoisomers thereof or pharmaceutically acceptable salts thereof, the use thereof for the preparation of therapeutic medicaments, pharmaceutical c
- -
-
Paragraph 720-722
(2017/02/24)
-
- Efficient Ruthenium(II)-Catalyzed Direct Reductive Amination of Aldehydes under Mild Conditions Using Hydrosilane as the Reductant
-
A direct reductive amination of aldehydes with anilines is performed with a ruthenium(II)-(arene) catalyst. The [RuCl2(p-cymene)]2/Ph2SiH2 catalytic system is very efficient for the synthesis of secondary amines and tertiary amines in good yields, and is highly chemoselective, tolerating a wide range of functional groups, such as NO2, CN, CO2Me, F, Cl, Br, OMe, Me, furyl and alkyl. We also report an interesting direductive amination of 2-ethylbutanal.
- Li, Bin,Zheng, Jianxiong,Zeng, Weifeng,Li, Yibiao,Chen, Lu
-
supporting information
p. 1349 - 1355
(2017/03/11)
-
- Tunable Triazole-Phosphine-Copper Catalysts for the Synthesis of 2-Aryl-1H-benzo[d]imidazoles from Benzyl Alcohols and Diamines by Acceptorless Dehydrogenation and Borrowing Hydrogen Reactions
-
Triazole-phosphine-copper complexes (TAP?Cu) have been synthesized and applied as tunable and efficient catalysts for the selective synthesis of fluoro-substituted 2-aryl-1H-benzo[d]imidazole and 1-benzyl-2-aryl-1H-benzo[d]imidazole derivatives from simple alcohols in only one step. TAP?Cu exhibited excellent and tunable catalytic activity for both dehydrogenation and borrowing hydrogen reactions with more than 80 examples being demonstrated for the first time. It was observed that the ligand played a critical role in catalyst activity. Mechanistic studies and deuterium labeling experiments indicated that the reactions proceeded by an initial and reversible alcohol dehydrogenation resulting in a copper hydride intermediate. This was also supported by the direct observation of a diagnostic copper hydride signal by solid-state infrared spectroscopy. The TAP?Cu-H complex showed absorptions at 912 cm?1 that could be assigned to copper?hydride stretches. Furthermore, the direct trapping of an intermediate bisimine was also successfully performed. (Figure presented.).
- Xu, Zhaojun,Wang, Duo-Sheng,Yu, Xiaoli,Yang, Yongchun,Wang, Dawei
-
supporting information
p. 3332 - 3340
(2017/10/06)
-
- Decarboxylative Aminomethylation of Aryl- and Vinylsulfonates through Combined Nickel- and Photoredox-Catalyzed Cross-Coupling
-
A mild approach for the decarboxylative aminomethylation of aryl sulfonates by the combination of photoredox and nickel catalysis through C?O bond cleavage is described for the first time. A wide range of aryl triflates as well as aryl mesylates, tosylates and alkenyl triflates afford the corresponding products in good to excellent yields.
- Fan, Lulu,Jia, Jiaqi,Hou, Hong,Lefebvre, Quentin,Rueping, Magnus
-
supporting information
p. 16437 - 16440
(2016/11/11)
-
- REDUCTION METHOD USING WATER AS PROTON SOURCE BY MEANS OF N-HETEROCYCLIC CARBENE
-
PROBLEM TO BE SOLVED: To provide a reduction method using water as a proton source by means of N-heterocyclic carbene, in which the N-heterocyclic carbene is used actively as a reaction accelerator to realize a hydrogenation reaction by using water as the proton source. SOLUTION: A solution, which is obtained by mixing: a reaction substrate shown at an upper stage of the following formulae; a precursor of the triazole-based N-heterocyclic carbene (NHC) shown at a lower stage; water; and 1,2-dimethoxyethane being a solvent, is reacted at 100°C or higher temperature for 2 hours or more while making the solution to pass through a microwave reaction unit and the reacted solution is subjected to reduced-pressure distillation to obtain a hydrogenated product. The formulae: (EWG1-EWG4 are each an ester group, a cyano group, a ketone group, an amido group or an imido group;R1-R5 are each a 1-20C aliphatic group, a 3-12C alicyclic group or 6-30C aromatic group) SELECTED DRAWING: None COPYRIGHT: (C)2016,JPO&INPIT
- -
-
Paragraph 0014; 0015; 0026; 0027
(2016/10/10)
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- An efficient catalytic reductive amination: A facile one-pot access to 1,2-dihydropyrrolo[3,4-b]indol-3(4H)-ones by using B(C 6 F 5 ) 3 /NaBH 4
-
An efficient combination of B(C6F5)3 and NaBH4 was developed for direct reductive amination of aldehydes. A wide range of functional groups such as ester, nitro, nitrile, halogen, alkene, heterocycles were tolerated. Also, acid sensitive protecting groups like TBDMS and TBDPS were not affected. In addition, the present methodology was extended for tandem amination-amidation of 3-formyl-indole-2-carboxylic acids with substituted anilines to afford 1,2-dihydropyrrolo[3,4-b]indol-3(4H)-ones. [Figure not available: see fulltext.]
- Nagarsenkar, Atulya,Prajapti, Santosh Kumar,Babu, Bathini Nagendra
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p. 711 - 716
(2015/06/17)
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- Modulators of methyl modifying enzymes, compositions and uses thereof
-
Agents for modulating methyl modifying enzymes, compositions and uses thereof are provided herein.
- -
-
Page/Page column 148; 149
(2015/12/26)
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- NOVEL COMPOUNDS FOR SELECTIVE HISTONE DEACETYLASE INHIBITORS, AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
-
The present invention relates to novel urea derivatives and, more particularly, to novel urea derivatives with histone deacetylase (HDAC) inhibitory activity, isomers thereof, pharmaceutically acceptable salts thereof, their use for the preparation of a medicaments comprising the same, a pharmaceutical composition comprising the same, a treatment method using the composition, and a method for preparing novel urea derivatives. The novel urea derivatives as selective histone deacetylase (HDAC) inhibitors are effective for the treatment of histone deacetylase-mediated diseases such as malignant tumors, inflammatory diseases, rheumatoid arthritis, neurodegeneration, etc.
- -
-
Paragraph 423; 424; 425
(2014/11/13)
-
- PROCESS FOR PREPARING AMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION IN THE PRESENCE OF A COMPLEX CATALYST COMPRISING IRIDIUM AND AN AMINO ACID
-
The invention relates to a process for preparing amines (A) by alcohol amination of alcohols (Al) by means of an aminating agent (Am) with elimination of water, wherein the alcohol amination is carried out in the presence of a complex catalyst comprising iridium and an amino acid.
- -
-
Paragraph 0147-0149
(2014/03/21)
-
- PHENYLETHYLPYRIDINE DERIVATIVES AS PDE4-INHIBITORS
-
The invention relates to novel compounds which are inhibitors of the phosphodiesterase 4 (PDE4) enzyme and muscarinic M3 receptor antagonists, methods of preparing such compounds, compositions containing them and therapeutic use thereof.
- -
-
Page/Page column 48; 49; 50
(2014/06/24)
-
- Efficient and chemoselective direct reductive amination of aromatic aldehydes catalyzed by oxo-rhenium complexes containing heterocyclic ligands
-
This work describes the catalytic activity of 17 oxo-rhenium complexes containing heterocyclic ligands in the direct reductive amination of 4-nitrobenzaldehyde with 4-chloroaniline, using phenylsilane as reducing agent. In general, all of the catalysts tested gave excellent yields of the secondary amine, although, the best result was obtained with the catalytic system PhSiH3/ReOBr2(Hhmpbta)(PPh3) (2.5 mol %). This system was also applied to the synthesis of a large variety of secondary amines in good to excellent yields and tertiary amines in moderate yields, with tolerance of different functional groups.
- Bernardo, Joana R.,Sousa, Sara C.A.,Florindo, Pedro R.,Wolff, Mariusz,Machura, Barbara,Fernandes, Ana C.
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p. 9145 - 9154
(2013/09/24)
-
- MODULATORS OF METHYL MODIFYING ENZYMES, COMPOSITIONS AND USES THEREOF
-
Agents for modulating methyl modifying enzymes, compositions and uses thereof are provided herein
- -
-
Paragraph 00289; 00290
(2013/06/05)
-
- Selective alkylation of amines with alcohols by Cp*- iridium(III) half-sandwich complexes
-
[Cp*Ir(Pro)Cl] (Pro = prolinato) was identified among a series of Cp*-iridium half-sandwich complexes as a highly reactive and selective catalyst for the alkylation of amines with alcohols. It is active under mild conditions in either toluene or water without the need for base or other additives, tolerates a wide range of alcohols and amines, and gives secondary amines in good to excellent isolated yields.
- Wetzel, Alexander,Woeckel, Simone,Schelwies, Mathias,Brinks, Marion K.,Rominger, Frank,Hofmann, Peter,Limbach, Michael
-
supporting information
p. 266 - 269
(2013/03/14)
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- Mechanistic investigation of the iridium-catalysed alkylation of amines with alcohols
-
The [Cp*IrCl2]2-catalysed alkylation of amines with alcohols was investigated using a combination of experimental and theoretical methods. A Hammett study involving a series of para-substituted benzyl alcohols resulted in a line with a negative slope. This clearly documents that a positive charge is built up in the transition state, which in combination with the measurement of a significant kinetic isotope effect determines hydride abstraction as being the selectivity-determining step under these conditions. A complementary Hammett study using para-substituted anilines was also carried out. Again, a line with a negative slope was obtained suggesting that nucleophilic attack on the aldehyde is selectivity-determining. A computational investigation of the entire catalytic cycle with full-sized ligands and substrates was performed using density functional theory. The results suggest a catalytic cycle where the intermediate aldehyde stays coordinated to the iridium catalyst and reacts with the amine to give a hemiaminal which is also bound to the catalyst. Dehydration to the imine and reduction to the product amine also takes place without breaking the coordination to the catalyst. The fact that the entire catalytic cycle takes place with all the intermediates bound to the catalyst is important for the further development of this synthetic transformation. The Royal Society of Chemistry 2012.
- Fristrup, Peter,Tursky, Matyas,Madsen, Robert
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supporting information; experimental part
p. 2569 - 2577
(2012/04/23)
-
- N-alkylation of amines with alcohols catalyzed by a water-soluble cp*iridium complex: An efficient method for the synthesis of amines in aqueous media
-
An efficient and environmentally benign catalytic system for the synthesis of various organic amines catalyzed by the water-soluble and air-stable (pentamethylcyclopentadienyl)-iridium-ammine iod- ide complex, [Cp*Ir(NH3)3][I]2 (Cp= pentamethylcyclopentadienyl), has been developed. A wide variety of secondary and tertiary amines were synthesized by the N-alkylation reactions of theoretical equivalents of amines with alcohols in water under air without a base. The synthesis of cyclic amines was also achieved by the N-alkylation of benzylamine with diols. Furthermore, the recycle use of the present water-soluble Cp*Ir catalyst was accomplished. Copyright
- Kawahara, Ryoko,Fujita, Ken-Ichi,Yamaguchi, Ryohei
-
supporting information; experimental part
p. 1161 - 1168
(2011/06/24)
-
- Highly chemoselective reductive amination by one pot reaction of aldehydes, amines and dihydropyridine catalyzed by TMSCl
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More efficient, cost effective and metal free DHP/TMSCl system for one pot reductive amination of aldehydes was developed. The method allows the efficient one pot synthesis of structurally diverse amines with Hantzsch ester as the hydrogen source in the presence of trimethylsilyl chloride as a catalyst in high to quantitative yields under mild conditions.
- Azizi,Amiri, A. R. Khajeh,Ghafuri,Saidi,Bolourtchian
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experimental part
p. 428 - 431
(2010/08/19)
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- Efficient and highly chemoselective direct reductive animation of aldehydes using the system silane/oxorhenium complexes
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This work reports a novel method for direct reductive amination of aldehydes with silanes catalyzed by several high-valent oxorhenium(V) and oxorhenium (VII) complexes. The catalytic system PhSiH3/ReIO 2(PPh3)2 (2.5mol%) was very efficient for the synthesis of secondary amines and highly chemoselective, tolerating a wide range of functional groups such as -NO2, -CF3, -SO 2R, -CO2R, -F, -Cl, -Br, -I, -CN, -OH, -OCH3, -SCH3, NCOR, and double bonds. This novel method was also employed in the synthesis of tertiary amines with moderate yields.
- Sousa, Sara C. A.,Fernandes, Ana C.
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experimental part
p. 2218 - 2226
(2010/11/05)
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- Reductive amination of aldehydes and ketones in a heterogeneous system in THF and under solvent-free conditions using sodium borohydride-silica phosphoric acid
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A chemoselective, fast, efficient, and high yielding method for the preparation of amines by reductive amination of aldehydes and ketones using sodium borohydride in the presence of silica phosphoric acid in THF and under solvent-free conditions at room temperature is described.
- Alinezhad, Heshmatollah,Tajbakhsh, Mahmoud,Ahangar, Roja Enayati
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- Cp*Ir-catalyzed N-alkylation of amines with alcohols. A versatile and atom economical method for the synthesis of amines
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A versatile and highly atom economical catalytic system consisting of [Cp*IrCl2]2/NaHCO3 (Cp*=pentamethylcyclopentadienyl) for the N-alkylation of amines with primary and secondary alcohols as alkylating reagents has been developed. For example, the reaction of equimolar amounts of aniline and benzyl alcohol in the presence of [Cp*IrCl2]2 (1.0 mol % Ir) and NaHCO3 (1.0 mol %) in toluene at 110 °C gives N-benzylaniline in 94% yield. The present catalytic system is applicable to the N-alkylation of both primary and secondary amines, and only harmless water is produced as co-product. A wide variety of secondary and tertiary amines can be synthesized with high atom economy under mild and less-toxic conditions. One-pot sequential N-alkylation leading to tertiary amines bearing three different substituents is also described.
- Fujita, Ken-ichi,Enoki, Youichiro,Yamaguchi, Ryohei
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p. 1943 - 1954
(2008/09/17)
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- Direct and indirect reductive amination of aldehydes and ketones with solid acid-activated sodium borohydride under solvent-free conditions
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A simple and convenient procedure for reductive amination of aldehydes and ketones using sodium borohydride activated by boric acid, p-toluenesulfonic acid monohydrate or benzoic acid as reducing agent under solvent-free conditions is described.
- Byung, Tae Cho,Sang, Kyu Kang
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p. 5725 - 5734
(2007/10/03)
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