- Defined Palladium-Phthalimidato Catalysts for Improved Oxidative Amination
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New palladium(II)-phthalimidato complexes have been synthesized, isolated, and structurally characterized. As demonstrated from over 30 examples, they constitute superior catalysts for oxidative amination reactions of alkenes with phthalimide as the nitrogen source. This work streamlines vicinal difunctionalization of alkenes and provides access to significantly improved and experimentally simplified synthetic protocols.
- Martínez, Claudio,Mu?iz, Kilian
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- Palladium-Catalyzed Carbonylative Dearomatization of Indoles
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An interesting palladium-catalyzed dearomative carbonylation of N-(2-bromobenzoyl)indoles has been developed. The catalytic system is composed of commercially available Pd(OAc)2 and DPPP and uses alcohols and anilines as nucleophiles to afford moderate to good yields of the desired products. This method provides a straightforward access to diverse fused indoline esters and amides with good functional group tolerance. Remarkably, this is the first example of carbonylative dearomatization.
- Wang, Hai,Wu, Xiao-Feng
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- Photoinduced reactions of 1,3,4(2H)-isoquinolinetriones with diphenylacetylenes - An efficient one pot syntheses of dibenz[de,g]-(2H)-isoquinoline-4, 6-dione derivatives
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Photoinduced reactions of 1,3,4(2H)-isoquinolinetriones with diphenylacetylenes afforded the corresponding dibenz[de,g]-(2H)-isoquinoline-4,6-dione derivatives in moderate to high yields via a reaction sequence involving [2+2] photocycloaddition, ring opening rearrangement of the oxetene intermediate and dehydrogenative cyclization in one pot. (C) 2000 Elsevier Science Ltd.
- Zhang,Qian,Fun,Xu
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- Improved synthesis of pyridazinediones under microwave irradiation
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Pyridazinediones have been synthesized with good to excellent yields under microwave irradiation. The results were compared with traditional stirring.
- Bourel, Line,Tartar, Andre,Melnyk, Patricia
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- Mechanistic Studies of Ullmann-Type C–N Coupling Reactions: Carbonate-Ligated Copper(III) Intermediates
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In Ullmann-type C?N coupling reactions, the involvement of CuIII species has been proposed many times on the basis of the oxidative addition–reductive elimination (OA-RE) path for these reactions, but actual species could not be traced in experimental studies. In the C?N coupling reactions, carbonate and phosphate were considered widely as bases. In the present study, Cu-mediated C?N coupling reactions of aryl halides and NuNH (amide and imide) were investigated extensively, and we provide direct spectroscopic evidence of actual CuIII species. For the first time, we reveal that carbonate and phosphate ions act as bidentate ligands as well as a base in the catalytic cycle, and thus the actual intermediate species is a carbonate- or phosphate-ligated, distorted octahedral CuIII complex. Our experimental and computational studies have strengthened the hypothesis that these reactions follow an OA-RE path.
- Gurjar, Kamlesh K.,Sharma, Rajendra K.
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- Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams
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An efficient and practical electrochemical method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature. The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by electric current and reaction time, and exhibits broad substrate scope and high functional group tolerance even to reduction-sensitive moieties. Initial mechanistic studies suggest that the approach heavily relies on the utilization of amines (e.g., i-Pr2NH), which are able to generate α-aminoalkyl radicals. This protocol provides an efficient route for the cleavage of C-O bonds under mild conditions with high chemoselectivity.
- Bai, Ya,Shi, Lingling,Zheng, Lianyou,Ning, Shulin,Che, Xin,Zhang, Zhuoqi,Xiang, Jinbao
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supporting information
p. 2298 - 2302
(2021/04/05)
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- A phosphonium ylide as a visible light organophotoredox catalyst
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A phosphonium ylide-based visible light organophotoredox catalyst has been designed and successfully applied to halohydrin synthesis using trichloroacetonitrile and epoxides. An oxidative quenching cycle by the ylide catalyst was established, which was confirmed by experimental mechanistic studies.
- Toda, Yasunori,Tanaka, Katsumi,Matsuda, Riki,Sakamoto, Tomoyuki,Katsumi, Shiho,Shimizu, Masahiro,Ito, Fuyuki,Suga, Hiroyuki
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supporting information
p. 3591 - 3594
(2021/04/14)
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- Visible-Light-Induced Controlled Oxidation of N-Substituted 1,2,3,4-Tetrahydroisoquinolines for the Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones and Isoquinolin-1(2H)-ones
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A visible light-rose bengal-TBHP mediated, controlled oxidation of N-substituted 1,2,3,4-tetrahydroisoquinolines is developed for the synthesis of 3,4-dihydroisoquinolin-1(2H)-ones and isoquinolin-1(2H)-ones. The present method feature's a broad substrate scope, good functional group tolerances, and the products were prepared in good to excellent yields. The developed methodology further demonstrated in the synthesis of isoindolo[2,1-b] isoquinolin-5(7H)-one (topoisomerase-I inhibitor). (Figure presented.).
- Bansode, Ajay H.,Suryavanshi, Gurunath
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supporting information
p. 1390 - 1400
(2021/01/26)
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- “On water” nano-Cu2O-catalyzed CO-free one-pot multicomponent cascade cyanation-annulation-aminolysis reaction toward phthalimides
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An efficient nano-Cu2O-catalyzed cascade multicomponent reaction of 2-halobenzoic acids and trimethylsilyl cyanide with diverse amines was developed using water as a solvent, affording versatileN-substituted phthalimide derivatives in moderate to excellent yields. This novel strategy features carbon monoxide gas-free, environmentally benign, one-pot multistep transformation, commercially available reagents, a cheap catalyst without any additives, wide functional group tolerance, and operational convenience.
- Wen, Xiaowei,Liu, Xiaojuan,Yang, Zhiqi,Xie, Menglan,Liu, Yuxi,Long, Lipeng,Chen, Zhengwang
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supporting information
p. 1738 - 1743
(2021/03/14)
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- High-throughput tandem-microwell assay for ammonia repositions FDA-Approved drugs to inhibit Helicobacter pylori urease
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To date, little attempt has been made to develop new treatments for Helicobacter pylori (H. pylori), although the community is aware of the shortage of treatments for H. pylori. In this study, we developed a 192-tandem-microwell-based high-throughput assay for ammonia that is a known virulence factor of H. pylori and a product of urease. We could identify few drugs, that is, panobinostat, dacinostat, ebselen, captan, and disulfiram, to potently inhibit the activity of ureases from bacterial or plant species. These inhibitors suppress the activity of urease via substrate-competitive or covalent-allosteric mechanism, but all except captan prevent the antibiotic-resistant H. pylori strain from killing human gastric cells, with a more pronounced effect than acetohydroxamic acid, a well-known urease inhibitor and clinically used drug for the treatment of bacterial infection. This study offers several bases for the development of new treatments for urease-containing pathogens and to study the mechanism responsible for the regulation of urease activity.
- Fang, Houqin,Huang, Shengshuo,Li, Fangzheng,Liao, Lujian,Liu, Fan,Liu, Qi,Wu, Fang,Wu, Xin-Yan,Xiao, Zhuping,Xu, Jinyi,Yu, Jing,Zhang, Yan-Xia,Zhou, Yueyang
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- Visible-Light-Induced Metal-/Photocatalyst-Free C-H Bond Imidation of Arenes
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In this study, a visible-light-induced intermolecular C-H bond imidation of arenes was achieved at ambient condition. By using simple phthalimide with (diacetoxyiodo)benzene and molecular iodine, direct metal-/photocatalyst-free C-N bond formation was achieved. The imidation protocol was designed by using time-dependent density functional theory calculations and experimentally demonstrated for 28 substrates with as high as 96% yield. Mechanistic studies indicated that radical-mediated aromatic substitution occurred via photolysis of N-iodophthalimide under visible-light irradiation.
- Kuribara, Takahito,Nakajima, Masaya,Nemoto, Tetsuhiro
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supporting information
p. 2235 - 2239
(2020/03/13)
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- One-Pot Three Component Synthesis of 2-(1H-Benzo[d]thiazole-2-yl)-N-Arylbenzamides in Glycerol Medium
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In this work, a series of 2-(1H-benzo[d]thiazole-2-yl)-N-arylbenzamides is synthesized by using diethyl phthalate, anilines and 2-amino-benzenethiol by one-pot three component synthesis in glycerol medium. Phosphoric acid is used as an effective reagent for this one-pot three component reaction. This reaction got completed in a short time, easy workup and gave an excellent yield in glycerol medium. The N-arylbenzamides was found to have significant cytotoxic potentials against various cancer cells viz., A549 (lung cancer), HeLa (cervical cancer) and MCF-7 (breast cancer) using MTT assay. The molecular docking study is also employed to understand the binding mechanism of N-arylbenzamides against the antibacterial target. The docking result shows the binding energy of compound 4a is -8.6 kcal/mol. The binding affinity is a major concern and it shows that Asn and Thr residues have an interaction with compound 4a.
- Thumula, Swathi,Srinivasadesikan, Venkatesan,Kottalanka, Ravi K.,Rajkumar, S. Rex Jeya,Ramchandran, Balajee
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p. 1343 - 1351
(2020/06/10)
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- Cu-catalyzed N-3-Arylation of Hydantoins Using Diaryliodonium Salts
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A general Cu-catalyzed, regioselective method for the N-3-arylation of hydantoins is described. The protocol utilizes aryl(trimethoxyphenyl)iodonium tosylate as the arylating agent in the presence of triethylamine and a catalytic amount of a simple Cu-salt. The method is compatible with structurally diverse hydantoins and operates well with neutral aryl groups or aryl groups bearing weakly donating/withdrawing elements. It is also applicable for the rapid diversification of pharmaceutically relevant hydantoins.
- Neerbye Berntsen, Linn,Nova, Ainara,Wragg, David S.,Sandtorv, Alexander H.
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supporting information
p. 2687 - 2691
(2020/04/10)
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- Organocatalyzed Synthesis of Highly Functionalized Phthalimides via Diels-Alder Reaction Employing Two Dienophiles
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An efficient and facile protocol for the synthesis of biologically and pharmaceutically important phthalimides is developed by l-proline-catalyzed reaction between two dienophiles of α,β-unsaturated aldehydes and maleimides. The reaction involves an efficient benzannulation that proceeds via a formal [4 + 2] cycloaddition of azadiene intermediates generated in situ from enals and N-substituted maleimides. This protocol provides a variety of functionalized phthalimide derivatives, including a potent COX-2 enzyme inhibitor.
- Akhtar, Muhammad Saeed,Lee, Yong Rok
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p. 15129 - 15138
(2020/12/02)
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- Tandem Reaction Approaches to Isoquinolones from 2-Vinylbenzaldehydes and Anilines via Imine Formation-6π-Electrocyclization-Aerobic Oxidation Sequence
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Two distinctive transition-metal-promoted aerobic oxidation protocols have been developed for the synthesis of isoquinolones from 2-vinylbenzaldehydes and aniline derivatives. Thus, the one-pot tandem reaction sequence of imine formation, thermal 6π-electrocyclization, followed by either Cu(OAc)2-mediated or Pd(OAc)2-catalyzed aerobic oxidation protocol allowed the ready access to isoquinolone derivatives. The control experiments revealed that the 1,2-dihydroisoquinoline intermediates from the 6π-electrocyclization of 1-azatrienes were aerobically oxidized to isoquinolones in the presence of either Cu(OAc)2 or Pd(OAc)2 catalyst.
- Lee, Jiyeon,Kim, Hun Young,Oh, Kyungsoo
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p. 474 - 478
(2020/01/21)
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- Synthesis of imides via palladium-catalyzed three-component coupling of aryl halides, isocyanides and carboxylic acids
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A palladium-catalyzed three-component synthesis of acyclic imides from feedstock aryl halides, carboxylic acids and isocyanides through the intermediacy of isoimides has been developed. The key to the success of this approach was controlled isocyanide slow addition and organic/aqueous biphasic conditions. This transition-metal-catalyzed approach features readily available starting materials, atom- and step-economy, good functional group compatibility and gram-scale synthetic capability. Utilization of this new method is illustrated in the late-stage functionalization of drugs Carprofen, Loxoprofen and Flurbiprofen. This strategy has also been successfully applied in the synthesis of cyclic imides including phthalimide, homophthalimide, and 2H-2-benzazepine-1,3-dione derivatives.
- Wang, Bo,He, Dan,Ren, Beige,Yao, Tuanli
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supporting information
p. 900 - 903
(2020/02/03)
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- Citric acid stabilized on the surface of magnetic nanoparticles as an efficient and recyclable catalyst for transamidation of carboxamides, phthalimide, urea and thiourea with amines under neat conditions
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Abstract: Citric acid-coated magnetic nanoparticles (Fe3O4–CA NPs) were successfully prepared and characterized. This magnetic nanocatalyst was employed as an efficient, recyclable, and environmentally benign heterogeneous catalyst for the transamidation of carboxamides, phthalimide, urea and thiourea with amines. Several derivatives of formylated and transamidated products were synthesized in good to excellent yields in the presence of this catalytic system. And, the catalyst could be easily separated from the reaction mixture using an external magnet and can be reused six times without any significant loss in its catalytic activity. Graphical abstract: [Figure not available: see fulltext.].
- Arefi, Marzban,Kazemi Miraki, Maryam,Mostafalu, Ramin,Satari, Mohammad,Heydari, Akbar
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p. 393 - 400
(2019/01/28)
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- Palladium Catalyzed Regioselective Synthesis of Substituted Biaryl Amides through Decarbonylative Arylation of Phthalimides
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The Pd(OAc)2 catalyzed cross-coupling of N-substituted phthalimides with aryl halide provides a single step direct access of a wide range of synthetically appealing ortho-substituted biarylamides in high yields through unique carbonyl (CO) replacement. The reaction proceeds through a ligand-free condition and is well tolerant to the diverse functionality of both imide and halide units. The reaction negates any requirement of organometallic reagent and needs a shorter reaction time and comparatively lower temperature as required for previously reported decarbonylative processes.
- Samanta, Partha Kumar,Biswas, Papu
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p. 3968 - 3976
(2019/03/26)
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- Ru-Catalyzed Selective C-H Bond Hydroxylation of Cyclic Imides
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We report on cyclic imides as weak directing groups for selective monohydroxylation reactions using ruthenium catalysis. Whereas acyclic amides are known to promote the hydroxylation of the C(sp2)-H bond enabling five-membered ring ruthenacycle intermediates, the cyclic imides studied herein enabled the hydroxylation of the C(sp2)-H bond via larger six-membered ruthenacycle intermediates. Furthermore, monohydroxylated products were exclusively obtained (even in the presence of overstoichiometric amounts of reagents), which was rationalized by the difficulty to accommodate coplanar intermediates once the first hydroxyl group was introduced into the substrate. The same reactivity was observed in the presence of palladium catalysts.
- Yuan, Yu-Chao,Bruneau, Christian,Dorcet, Vincent,Roisnel, Thierry,Gramage-Doria, Rafael
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p. 1898 - 1907
(2019/02/05)
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- Ruthenium(ii)-catalysed selective C(sp2)-H bond benzoxylation of biologically appealing: N -arylisoindolinones
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Site- and regio-selective aromatic C-H bond benzoxylations were found to take place using biologically appealing N-arylisoindolinones under ruthenium(ii) catalysis in the presence of (hetero)aromatic carboxylic acid derivatives as coupling partners. Besides the presence of two potential C(sp2)-H sites available for functionalization in the substrates, exclusive ortho selectivity was achieved in the phenyl ring attached to the nitrogen atom. Notably, the reactions occurred in a selective manner as only mono-functionalized products were formed and they tolerated a large number of functional chemical groups. The ability of the cyclic tertiary amide within the isoindolinone skeleton to act as a weak directing group in order to accommodate six-membered ring ruthenacycle intermediates appears to be the key to reach such high levels of selectivity. In contrast, the more sterically demanding cyclic imides were unreactive under identical reaction conditions.
- Yuan, Yu-Chao,Bruneau, Christian,Roisnel, Thierry,Gramage-Doria, Rafael
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p. 7517 - 7525
(2019/08/20)
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- Site-Selective Ruthenium-Catalyzed C-H Bond Arylations with Boronic Acids: Exploiting Isoindolinones as a Weak Directing Group
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Biologically relevant N-arylisoindolinones efficiently underwent arylation reactions under ruthenium catalysis via C-H bond functionalization. The reactions exclusively led to monoarylated products, and only ortho selectivity was observed in the aromatic ring connected to the nitrogen atom. Interestingly, no C-H bond functionalization was observed in the other benzene ring in the ortho position with respect to the carbonyl group. This ruthenium-catalyzed reaction displayed a high functional group tolerance, and it employed readily available and benchmark stable boronic acid and potassium aryltrifluoroborate derivatives as coupling partners. An appealing late-stage functionalization of indoprofen applying this methodology is showcased.
- Yuan, Yu-Chao,Bruneau, Christian,Roisnel, Thierry,Gramage-Doria, Rafael
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p. 12893 - 12903
(2019/09/13)
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- Synthesis, molecular docking, cytotoxicity and antioxidant activity evaluation of isoindoline-1,3-dione derivatives
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A variety of amines have been employed to functionalize isobenzofuran-1,3-dione to obtain isoindoline-1,3-dione derivatives in the base free conditions. All the synthesized compounds are screened for their bioactivity through molecular docking, cytotoxicity (against HeLa) and antioxidant activity. ABTS and DPPH are employed to assess the antioxidant activity. Among the synthesized isoindoline-1,3-dione derivatives (3a-k), compound 3e has showed the best antioxidant activity and also exhibited better binding energy when docked with caspase-3 protein. Cytotoxicity of the synthesized compounds was studied against cervical cancer cell line (HeLa) and compound 3e has displayed better activity than other isoindoline derivatives.
- Kumar, Palanichamy Santhosh,Kumar, Kuruba Bharath,Obadiah, Asir,Kumar, Suluvoy Jagadish,Mohanapriya, Raman,Durairaj, Arulappan,Ramanathan, Subramanian,Vasanthkumar, Samuel
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p. 2548 - 2556
(2019/10/02)
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- Br?nsted acid mediated intramolecular cyclopropane ring expansion/[4 + 2]-cycloaddition
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A cascade reaction of 3-hydroxy-2-phenylisoindolin-1-one and cyclopropyl ketone has been developed via a Br?nsted acid-promoted ring-opening/intramolecular cross-cycloaddition/[4 + 2]-cycloaddition process. The developed methodology provides straightforward access to pentacyclic isoindolin-1-one derivatives under simple reaction conditions.
- Li, Jian,Zhu, Shangrong,Xu, Qiuneng,Liu, Li,Yan, Shenghu
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p. 10004 - 10008
(2019/12/23)
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- C?N Cross-Coupling Reactions Under Mild Conditions Using Singlet Di-Radical Nickel(II)-Complexes as Catalyst: N-Arylation and Quinazoline Synthesis
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Herein we report a cost-effective synthetic approach for C?N cross-coupling reactions of a broad array of nitrogen nucleophiles and aryl halides under mild conditions. These reactions are catalyzed by an inexpensive, air-stable, earth-abundant and easy-to-prepare singlet di-radical nickel(II)-catalyst containing two antiferromagnetically coupled single-electron oxidized diiminosemiquinonato type ligands. This protocol provides an alternative method for C?N cross-coupling reactions avoiding nickel(0)/nickel(II) or nickel(I)/nickel(III) redox processes via cooperative participation of metal and ligand-centered redox events. Besides a wide range of N-arylation reactions, by judicious choice of aryl halides and nitrogen nucleophiles the synthesis of a variety of polysubstituted quinazolines has been achieved in moderate to good yields under relatively mild reaction conditions. Our catalyst has been found to be almost equally effective in quinazoline synthesis via C?N cross-coupling of (i) 2-bromobenzylamine with benzamide, and (ii) 2-bromobenzylbromide with amidine. Control experiments and DFT studies were performed to improve the understanding of the cooperative participation of ligand and metal (nickel)-centered redox events during oxidative addition/reductive elimination processes of the catalytic cycle and to shed light on the plausible mechanistic pathway of the C?N cross-coupling reactions. (Figure presented.).
- Sikari, Rina,Sinha, Suman,Chakraborty, Gargi,Das, Siuli,van Leest, Nicolaas Petrus,Paul, Nanda D.
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supporting information
p. 4342 - 4353
(2019/08/21)
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- PPh3/I2/HCOOH: An efficient CO source for the synthesis of phthalimides
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A straightforward and general method has been developed for the synthesis of phthalimide derivatives from 2-iodobenzamides and PPh3/I2/HCOOH in the presence of a catalytic amount of Pd(OAc)2. The reaction results demonstrate that PPh3/I2/HCOOH is a facile, efficient and safe CO source. The whole process is carried out in toluene at 80 °C and furnishes the desired products in good to excellent yields.
- Wang, Yingying,Zhou, Yang,Lei, Min,Hou, Jinjun,Jin, Qinghao,Guo, Dean,Wu, Wanying
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supporting information
p. 1180 - 1185
(2019/01/26)
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- Aerobic Acyloxylation of Allylic C?H Bonds Initiated by a Pd0 Precatalyst with 4,5-Diazafluoren-9-one as an Ancillary Ligand
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Palladium-catalyzed allylic C?H oxidation has been widely studied, but most precedents use acetic acid as the coupling partner. In this study, a method compatible with diverse carboxylic acid partners has been developed. Use of a Pd0 precatalyst under aerobic reaction conditions leads to oxidation of Pd0 by O2 in the presence of the desired carboxylic acid to generate a PdII dicarboxylate that promotes acyloxylation of the allylic C?H bond. Good-to-excellent yields are obtained with a roughly 1:1 ratio of the alkene and carboxylic acid reagents. Optimized reaction conditions employ 4,5-diazafluoren-9-one (DAF) as a ligand, in combination with a quinone/iron phthalocyanine cocatalyst system to support aerobic catalytic turnover.
- Kozack, Caitlin V.,Sowin, Jennifer A.,Jaworski, Jonathan N.,Iosub, Andrei V.,Stahl, Shannon S.
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p. 3003 - 3007
(2019/06/17)
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- A NOVEL PROCESS FOR THE PREPARATION OF HIV PROTEASE INHIBITOR AND INTERMEDIATES THEREOF
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The present invention relates to process for the preparation of Darunavir or a solvate thereof of Formula (I) using a novel intermediate (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (2S,3R)-4-(4-(1,3-dioxoisoindolin-2-yl)-N-isobutylphenylsulfonamido)-3 -hydroxy- 1 -phenylbutan-2- ylcarbamate Compound of formula (II): The present invention also relates to the process for the preparation of novel intermediates (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (2S,3R)-4-(4-(l,3-dioxo iso indolin-2-yl)-N-isobutylphenylsulfonamido)-3 -hydroxy-1-phenylbutan-2-ylcarbamate Compound of formula (II). Darunavir or its solvate of formula (I) are useful therapeutic agent and used in treatment of antiviral diseases.
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Page/Page column 16
(2018/02/16)
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- The aminocarbonylation of 1,2-diiodoarenes with primary and secondary amines catalyzed by palladium complexes with imidazole ligands
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The efficient carbonylative cyclization of 1,2-diiodobenzene with different primary and secondary amines was performed using a palladium complex with an imidazole ligand, PdCl2(BIM)2, as a catalyst. In reactions performed at 1 atm of CO with primary amines, phthalimides were obtained as the only products with yields of up to 100% in 4 h. An even shorter time, 1 h, was sufficient to obtain the same products employing methyl-2-iodobenzoate as a substrate instead of 1,2-diiodobenzene. In an analogous reaction with secondary amines, 1,2-diiodobenzene was converted to three products, formed in amounts dependent on the reaction conditions. The presence of Pd NPs and soluble palladium intermediates indicated their participation in the catalytic reaction.
- Wójcik, Przemys?aw,Trzeciak, Anna M.
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- L -Proline-Catalyzed Synthesis of Phthalimide Derivatives and Evaluation of Their Antioxidant, Anti-Inflammatory, and Lipoxygenase Inhibition Activities
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A study was planned to synthesize the phthalimide derivatives as phthalimides have versatile biological activities. To synthesize the phthalimide derivatives, initially the reaction was optimized with various catalysts, and L-proline was found to be the best catalyst as it provided excellent yield. A series of phthalimide derivatives was synthesized by facile one-top reaction of phthalic acid with aryl amines under mild reaction conditions in the presence of L-proline as catalyst. Products were obtained in excellent yields and structurally characterized by 1H, 13C NMR, and mass spectral data. Products 1-7 were evaluated for antioxidant, anti-inflammatory, and lipoxygenase enzyme inhibition activities. Compounds 1 and 4 showed potent antioxidant activity under DPPH with IC50 values 27.3 and 25.0 μM when compared with the standard BHA (IC50 = 44.2 μM), respectively. Compounds 1 and 4 further showed strong lipoxygenase inhibition activity with IC50 values 21.34 and 20.45 μM when compared with standard baicalein (IC50 = 22.60 μM), respectively. Compound 2 was found to be promising and about equal to the used standard aspirin in the inhibition of bovine serum albumin denaturation, while other compounds showed weak-to-moderate % inhibition.
- Perveen, Shagufta,Orfali, Raha
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- A method for utilizing the carbonylation reaction one-pot synthesis N - substituted phthalimide method
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The invention relates to a one-pot method for synthesizing N-substituted phthalimide through carbonylation. The method comprises the following steps: adding aromatic aldehyde, amine, a metal palladium catalyst and a solvent into a reaction container, then adding a copper salt as an oxidizing agent and carrying out stirring for 4 to 24 h at normal temperature; sleeving the reaction container with a balloon filled with carbon monoxide and oxygen and carrying out a stirring reaction at 40 to 150 DEG C for 12 to 72 h; after completion of the reaction, carrying out cooling to room temperature and dismounting the balloon; subjecting a reaction solution to filtering and carrying out pressure reduced evaporation to remove a solvent so as to obtain a crude product; and subjecting the crude product to column chromatographic purification so as to obtain the N-substituted phthalimide. The one-pot method for synthesizing N-substituted phthalimide through carbonylation is simple and safe to operate, uses easily available and cheap raw materials, has good function group applicability and can be used for synthesis of a plurality of drug molecules; and the method has excellent yield, is favorable for industrial production and has important application values in organic synthesis.
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Paragraph 0169; 0170
(2018/02/04)
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- Carbonylation Access to Phthalimides Using Self-Sufficient Directing Group and Nucleophile
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Herein we report a novel palladium-catalyzed oxidative carbonylation reaction for the synthesis of phthalimides with high atom- and step-economy. In our strategy, the imine and H2O, which are generated in situ from the condensation of aldehyde and amine, serve as self-sufficient directing group and nucleophile, respectively. This method provides rapid access to phthalimides starting from readily available materials in a one-pot manner. Various phthalimide derivatives are constructed efficiently, including medicinally and biologically active phthalimide-containing compounds.
- Ji, Fanghua,Li, Jianxiao,Li, Xianwei,Guo, Wei,Wu, Wanqing,Jiang, Huanfeng
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p. 104 - 112
(2018/02/19)
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- Radical Trifluoromethoxylation of Arenes Triggered by a Visible-Light-Mediated N?O Bond Redox Fragmentation
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A simple trifluoromethoxylation method enables non-directed functionalization of C?H bonds on a range of substrates, providing access to aryl trifluoromethyl ethers. This light-driven process is distinctly different from conventional procedures and occurs through an OCF3 radical mechanism mediated by a photoredox catalyst, which triggers an N?O bond fragmentation. The pyridinium-based trifluoromethoxylation reagent is bench-stable and provides access to synthetic diversity in lead compounds in an operationally simple manner.
- Jelier, Benson J.,Tripet, Pascal F.,Pietrasiak, Ewa,Franzoni, Ivan,Jeschke, Gunnar,Togni, Antonio
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supporting information
p. 13784 - 13789
(2018/09/14)
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- Method for constructing N-phenylphthalimide in one step from imine as starting material
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The invention discloses a method for constructing N-phenylphthalimide in one step from imine as a starting material. According to the method, (E)-N,1-diphenylmethylimine is used as a reaction raw material and subjected to carbonylation reaction, and N-phenylphthalimide is constructed in one step. The method has the characteristics of mild reaction conditions, simple operation process and excellentyield.
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Paragraph 0022-0046
(2019/01/16)
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- Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives
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The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.
- Yuan, Yu-Chao,Kamaraj, Raghu,Bruneau, Christian,Labasque, Thierry,Roisnel, Thierry,Gramage-Doria, Rafael
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p. 6404 - 6407
(2017/12/08)
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- Phthalimide-N-sulfonic acid, an efficient catalyst for the synthesis of various isoindoline-1,3-dione derivatives
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An environmentally friendly method is described for the synthesis of various isoindoline-1,3-dione derivatives from the reaction of phthalic anhydride with aromatic/aliphatic amines in ethanol at 80 °C by phthalimide-N-sulfonic acid as an efficient heterogeneous acid catalyst. Some advantages include the metal-free and environmentally friendly protocol, simple operation and reusable processes, easy recovery, short reaction times, and high yields.
- Habibi, Davood,Pordanjani, Hossein Mohammadkhani
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p. 2293 - 2299
(2017/10/05)
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- Synthesis and molecular docking studies of some 4-phthalimidobenzenesulfonamide derivatives as acetylcholinesterase and butyrylcholinesterase inhibitors
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A series of 4-phthalimidobenzenesulfonamide derivatives were designed, synthesized and evaluated for the inhibitory activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Structures of the title compounds were confirmed by spectral and elemental analyses. The cholinesterase (ChE) inhibitory activity studies were carried out using Ellman’s colorimetric method. The biological activity results revealed that all of the title compounds (except for compound 8) displayed high selectivity against AChE. Among the tested compounds, compound 7 was found to be the most potent against AChE (IC50= 1.35 ± 0.08 μM), while compound 3 exhibited the highest inhibition against BuChE (IC50= 13.41 ± 0.62 μM). Molecular docking studies of the most active compound 7 in AChE showed that this compound can interact with both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE.
- Soyer, Zeynep,Uysal, Sirin,Parlar, Sulunay,Tarikogullari Dogan, Ayse Hande,Alptuzun, Vildan
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- PdII/AgI-Catalyzed Room-Temperature Reaction of γ-Hydroxy Lactams: Mechanism, Scope, and Antistaphylococcal Activity
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The present work reports a PdII/AgI-promoted amidoalkylation reaction involving various γ-hydroxy lactams and C/O/S nucleophiles at room temperature. The dual mode of activation of both the electrophile and nucleophile by in situ generated catalytically active cationic PdII species facilitates the reaction at room temperature. Among the synthesized isoindoline derivatives, three compounds are found to be active against vancomycin and methicillin-resistant S. aureus strain with appreciable MIC values.
- Dutta, Manali,Mandal, Santi M.,Pegu, Rupa,Pratihar, Sanjay
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p. 2193 - 2198
(2017/03/01)
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- Chan-Lam-Type C-N Cross-Coupling Reactions under Base- and Ligand-Free CuI-Zeolite Catalysis
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Various representative copper(I)-exchanged zeolites were investigated for their catalytic potential in Chan-Lam cross-coupling reactions. CuI-USY appeared as the best catalyst and proved to efficiently promote C-N cross-coupling processes under attractive, simple, and practical conditions, namely refluxing in methanol under air and without any base.
- Garnier, Tony,Sakly, Randa,Danel, Mathieu,Chassaing, Stefan,Pale, Patrick
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supporting information
p. 1223 - 1230
(2017/03/11)
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- Synthetic method for N-substituted imide
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The invention provides a synthetic method for N-substituted imide. According to the method, aromatic ketone and amine are used as substrates, air or oxygen is used as an oxygen source, and cyclic imide is produced under liquid phase conditions under the action of a catalyst. The method is mild in conditions, high in oxidation efficiency and high in product yield; and since the method uses air or oxygen as the oxygen source, the method is economic and environment-friendly and has good application prospect.
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Paragraph 0016; 0027; 0018; 0019; 0020
(2017/04/20)
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- Efficient copper-catalyzed N-arylation of NH-containing heterocycles and sulfonamides with arenediazonium tetrafluoroborates
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A practical copper-catalyzed N-arylation of NH-containing heterocycles with arenediazonium tetrafluoroborates has been developed using CuCl as catalyst and K2CO3 as additive under ligand-free conditions. This reaction system has wide substrate scope including imides, 1H-pyrazole, 1H-tetrazoles, 1,2-benzisothiazol-3(2H)-one, and related sulfonamides and gives moderate to excellent yields (up to 95%) of the desired products. This strategy is very general, simple, environmentally friendly, and tolerant of oxygen.
- Ouyang, Yu-Qing,Yang, Zhen-Hua,Chen, Zhong-Hui,Zhao, Sheng-Yin
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supporting information
p. 771 - 778
(2017/04/06)
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- Palladium-Catalyzed Synthesis of 1H-Indenes and Phthalimides via Isocyanide Insertion
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A new and versatile multicomponent domino strategy has been developed for the synthesis of a series of 1H-indene and phthalimide derivatives from simple and readily available starting materials. This process operating under mild conditions shows a broad substrate scope with moderate to excellent yields.
- Wang, Xu,Xiong, Wenfang,Huang, Yubing,Zhu, Jiayi,Hu, Qiong,Wu, Wanqing,Jiang, Huanfeng
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p. 5818 - 5821
(2017/11/10)
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- Transamidation of primary carboxamides, phthalimide, urea and thiourea with amines using Fe(OH)3@Fe3O4 magnetic nanoparticles as an efficient recyclable catalyst
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The highly efficient transamidation of primary amides, phthalimide, urea and thiourea with amines catalyzed by magnetic Fe(OH)3@Fe3O4 nanoparticles is described. This magnetic nanocomposite is able to catalyze transamidation reactions of a wide range of the above-mentioned substrates with amines, generating a new amide bond in moderate to good yields. The catalyst exhibited very good recyclability and reusability up to five runs without significant loss of its catalytic activity.
- Arefi, Marzban,Heydari, Akbar
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p. 24684 - 24689
(2016/03/16)
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- METHODS OF MANUFACTURE OF 2-HYDROCARBYL-3,3-BIS(HYDROXYARYL)PHTHALIMIDINES
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A method for the manufacture of a 2-hydrocarbyl-3,3-bis(hydroxyaryl)phthalimidine composition comprises: reacting a phthalimide of formula (2) with a phenol of formula (3) I (2) I (3) in the presence of a catalyst and optionally a solvent at an elevated temperature to form the 2-hydrocarbyl-3,3-bis(hydroxyaryl)phthalimidine composition, wherein the 2-hydrocarbyl-3,3-bis(hydroxyaryl)phthalimidine composition comprises a 2-hydrocarbyl-3,3-bis(hydroxyaryl)phthalimidine of formula (1) I (1) wherein in formulas (1), (2) and (3), R1 is hydrogen, C1-6 alkyl, C1-6 alkoxy, or phenyl optionally substituted with 1 to 5 C1-6 alkyls, each occurrence of R2 and R3 is independently a C1-6 alkyl, and p and q are independently 0 to 4.
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Paragraph 0089
(2016/12/16)
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- Facile synthesis of 3-substituted isoindolinones Dedicated to the memory of Professor Sharon Roscoe, a colleague and mentor instrumental in shaping the careers of many chemists
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The reactions of N-aryl-3-hydroxyisoindolinones and alkyl aryl ketones under Lewis acid-catalyzed anhydrous conditions afforded the corresponding substituted isoindolinones in good to excellent yields.
- Al-Jaroudi, Zainab,Mohapatra, Prabhu P.,Jha, Amitabh
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supporting information
p. 772 - 777
(2016/02/05)
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- A facile and practical copper diacetate mediated, ligand free C-N cross coupling of trivalent organobismuth compounds with amines and N-heteroarenes
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In present work, an efficient Cu(OAc)2·H2O catalyzed protocol in the absence of any additional ligand has been developed for the N-arylation of amines and nitrogen containing heterocycles using trivalent organobismuth reagents under mild conditions. This protocol tolerates a variety of functional groups on amines and the organobismuth reagent with a high degree of chemoselectivity.
- Jadhav,Pardeshi
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p. 14531 - 14537
(2016/02/19)
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- Stable and Reusable Binaphthyl-Supported Palladium Catalyst for Aminocarbonylation of Aryl Iodides
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A binaphthyl-supported Pd nanoparticles (Pd-BNP)-catalyzed aminocarbonylation of aryl iodides in the presence of carbon monoxide and amines for the synthesis of amides has been developed. This methodology provides an efficient route for the synthesis of a COX-2 enzyme inhibitor having anti-inflammatory activity.
- Sharma, Nidhi,Sekar, Govindasamy
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p. 314 - 320
(2016/02/14)
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- Sterically Congested 2,6-Disubstituted Anilines from Direct C?N Bond Formation at an Iodine(III) Center
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2,6-Disubstituted anilines are readily prepared from the direct reaction between amides and diaryliodonium salts. As demonstrated for 24 different examples, the reaction is of unusually broad scope with respect to the sterically congested arene and the nitrogen source, occurs without the requirement for any additional promoter, and proceeds through a direct reductive elimination at the iodine(III) center. The efficiency of the coupling procedure is further demonstrated within the short synthesis of a chemerin binding inhibitor.
- Lucchetti, Nicola,Scalone, Michelangelo,Fantasia, Serena,Mu?iz, Kilian
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supporting information
p. 13335 - 13339
(2016/10/30)
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- Synthesis of Amides and Phthalimides via a Palladium Catalyzed Aminocarbonylation of Aryl Halides with Formic Acid and Carbodiimides
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A novel method for the preparation of amides and phthalimides has been developed. The process involves a palladium catalyzed aminocarbonylation of an aryl halide, using a carbodiimide and formic acid as the carbonyl source. Experimental data suggest that the mechanistic pathway for this process involves in-situ generation of carbon monoxide from the reaction of formic acid with a carbodiimide in the presence of a palladium catalyst. The method can be used to produce a variety of amides and N-substituted phthalimides efficiently.
- Seo, Yong-Sik,Kim, Dong-Su,Jun, Chul-Ho
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supporting information
p. 3508 - 3512
(2016/12/26)
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- Cuprous Oxide Catalyzed Oxidative C-C Bond Cleavage for C-N Bond Formation: Synthesis of Cyclic Imides from Ketones and Amines
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Selective oxidative cleavage of a C-C bond offers a straightforward method to functionalize organic skeletons. Reported herein is the oxidative C-C bond cleavage of ketone for C-N bond formation over a cuprous oxide catalyst with molecular oxygen as the oxidant. A wide range of ketones and amines are converted into cyclic imides with moderate to excellent yields. In-depth studies show that both α-C-H and β-C-H bonds adjacent to the carbonyl groups are indispensable for the C-C bond cleavage. DFT calculations indicate the reaction is initiated with the oxidation of the α-C-H bond. Amines lower the activation energy of the C-C bond cleavage, and thus promote the reaction. New insight into the C-C bond cleavage mechanism is presented.
- Wang, Min,Lu, Jianmin,Ma, Jiping,Zhang, Zhe,Wang, Feng
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p. 14061 - 14065
(2016/01/25)
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- A metal-free approach for transamidation of amides with amines in aqueous media
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An efficient, environmentally benign and a mild protocol for transamidation of amides with a variety of amines in the presence of K2S2O8 using stoichiometric quantity in aqueous conditions has been established. This method works under conventional thermal conditions and in microwave irradiation as well. A series of amides have been prepared using this reaction and this is a greener protocol for transamidation, which offers a diverse kind of substrate scope with exclusive product formation (yields 90-98%).
- Srinivas, Mahesuni,Hudwekar, Abhinandan D.,Venkateswarlu, Vunnam,Reddy, G. Lakshma,Kumar, K. A. Aravinda,Vishwakarma, Ram A.,Sawant, Sanghapal D.
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supporting information
p. 4775 - 4779
(2015/07/20)
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- METHODS OF MANUFACTURE OF 2-HYDROCARBYL-3,3-BIS(HYDROXYARYL)PHTHALIMIDINES
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A method for the manufacture of a 2-hydrocarbyl-3,3-bis(hydroxyaryl)phthalimidine composition comprises: reacting a phthalimide of formula (2) with a phenol of formula (3) I (2) I (3) in the presence of a catalyst and optionally a solvent at an elevated temperature to form the 2- hydrocarbyl-3,3-bis(hydroxyaryl)phthalimidine composition, wherein the 2-hydrocarbyl-3,3- bis(hydroxyaryl)phthalimidine composition comprises a 2-hydrocarbyl-3,3- bis(hydroxyaryl)phthalimidine of formula (1) I (1) wherein in formulas (1), (2) and (3), R1 is hydrogen, C1-6 alkyl, C1-6 alkoxy, or phenyl optionally substituted with 1 to 5 C 1-6 alkyls, each occurrence of R2 and R3 is independently a C1-6 alkyl, and p and q are independently 0 to 4.
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Paragraph 0100
(2015/08/03)
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