- PhICl2/NH4SCN-Mediated Oxidative Regioselective Thiocyanation of Pyridin-2(1H)-ones
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The reaction of pyridin-2(1H)-ones with PhICl2 and NH4SCN enables an efficient regioselective thiocyanation, leading to the synthesis of the biologically interesting C5 thiocyanated 2-pyridones in good to high yields. The mechanistic pathway of this metal-free approach is postulated to involve the formation of the reactive thiocyanogen chloride from the reaction of PhICl2 and NH4SCN followed with the regioselective electrophilic thiocyanation of the pyridin-2(1H)-one ring.
- Tao, Shanqing,Xiao, Jiaxi,Li, Yadong,Sun, Fengxia,Du, Yunfei
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- C-H Pyridonation of (Hetero-)Arenes by Pyridinium Radical Cations
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Pyridones are important heteroaromatic scaffolds found in natural products and pharmaceuticals and are, therefore, of major interest in organic synthetic chemistry. Here we report the first C-H pyridonation of unactivated (hetero-)arenes, providing a methodology to directly access N-aryl-2- and 4-pyridones. Generation of pyridinium radical cations through single-electron reduction allows for the synthesis of pyridones on structurally complex molecules.
- Hillenbrand, Julius,Ham, Won Seok,Ritter, Tobias
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Read Online
- Structure Ligation Relationship of Amino Acids for the Amination Cross-Coupling Reactions
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The structure ligation relationship (SLR) of amino acids (AAs) for the cross-coupling aminations was examined. While AA ligated C-N cross-couplings under Pd and Ni catalysis were minor or ineffective, the AA ligated Cu-catalyzed C-N cross-couplings were promising particularly with the use of l-methionine. The roles of -NH2, -CO2H, and -S- of l-methionine were investigated and found critical for their ligation efficiency. The finding was compatible with aromatic as well as aliphatic amines including tautomerizable N-heteroarenes.
- Vaidya, Gargi Nikhil,Khan, Arif,Verma, Hansa,Kumar, Sanjeev,Kumar, Dinesh
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- Synthesis of N-aryl pyridin-2-ones via ligand coupling reactions using pentavalent organobismuth reagents
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An efficient method for the synthesis of N-aryl pyridin-2-ones was established by way of ligand coupling reactions using pentavalent organobismuth reagents such as triarylbismuth dichlorides. Copyright
- Ikegai, Kazuhiro,Mukaiyama, Teruaki
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- An unusual rearrangement involving 5-bromo-1-phenylpyridone during its methyl cross coupling with turbo-Grignard reagent, leading to a 5-bromopyridone-fused seven-membered carbocyclic ring
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[Figure not available: see fulltext.] The structure of a cyclohepta[c]pyridin-1-one, a product of an unusual transformation, isolated during a turbo-Grignard reagentpromoted methyl cross coupling to 5-bromo-1-phenyl-2-pyridone, was determined by 1H and 13C NMR, COSY and high-resolution MS, as well as computer modeling. Its formation suggests a remarkable nucleophilic attack at the α-position to the pyridone carbonyl group. A rational pathway is presented.
- Falb, Eliezer,Ulanenko, Konstantin,Tor, Andrey,Afri, Michal,Gottlieb, Hugo,Hassner, Alfred
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Read Online
- Manganese-Promoted Regioselective Direct C3-Phosphinoylation of 2-Pyridones
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A highly efficient and regioselective manganese-induced radical oxidative direct C?P bond formation between 2-pyridones and secondary phosphine oxides was developed. The C3-selective phosphinoylation was conveniently achieved through a combination of substoichiometric manganese and persulfate oxidant under mild conditions. Various 3-phosphinoylated pyridone products can be obtained in moderate to high yields. Preliminary mechanistic studies suggest that the reaction is likely to involve a radical pathway induced by catalytically active Mn3+ species.
- Chantarojsiri, Teera,Kittikool, Tanakorn,Phakdeeyothin, Kunita,Yotphan, Sirilata
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supporting information
p. 3071 - 3078
(2021/07/22)
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- Activated charcoal supported copper nanoparticles: A readily available and inexpensive heterogeneous catalyst for the N-arylation of primary amides and lactams with aryl iodides
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A novel heterogeneous copper catalyst has been developed by supporting copper nanoparticles on activated charcoal via in situ reducing copper(II) with aqueous hydrazine as reductant. The characterization of Cu/C catalyst showed that the Cu0 nano-particles were formed on the surface of charcoal. This catalyst displayed good catalytic activities toward the N-arylation of primary amides and lactams with aryl iodides.
- Zhao, Rong,Dong, Wenwen,Teng, Jiangge,Wang, Zhiwei,Wang, Yunzhong,Yang, Jianguo,Jia, Qiang,Chu, Changhu
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supporting information
(2020/12/21)
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- Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis
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The value of catalytic dehydrogenation of aliphatics (CDA) in organic synthesis has remained largely underexplored. Known homogeneous CDA systems often require the use of sacrificial hydrogen acceptors (or oxidants), precious metal catalysts, and harsh reaction conditions, thus limiting most existing methods to dehydrogenation of non- or low-functionalized alkanes. Here we describe a visible-light-driven, dual-catalyst system consisting of inexpensive organophotoredox and base-metal catalysts for room-temperature, acceptorless-CDA (Al-CDA). Initiated by photoexited 2-chloroanthraquinone, the process involves H atom transfer (HAT) of aliphatics to form alkyl radicals, which then react with cobaloxime to produce olefins and H2. This operationally simple method enables direct dehydrogenation of readily available chemical feedstocks to diversely functionalized olefins. For example, we demonstrate, for the first time, the oxidant-free desaturation of thioethers and amides to alkenyl sulfides and enamides, respectively. Moreover, the system's exceptional site selectivity and functional group tolerance are illustrated by late-stage dehydrogenation and synthesis of 14 biologically relevant molecules and pharmaceutical ingredients. Mechanistic studies have revealed a dual HAT process and provided insights into the origin of reactivity and site selectivity.
- Zhou, Min-Jie,Zhang, Lei,Liu, Guixia,Xu, Chen,Huang, Zheng
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supporting information
p. 16470 - 16485
(2021/10/20)
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- Light-induced [2 + 2] cycloadditions for the construction of cyclobutane-fused pyridinyl sulfonyl fluorides
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Cyclobutanes are an important class of motifs present in a wide range of natural products and other biologically significant molecules. A photocatalytic [2 + 2] cycloaddition between pyridones or isoquinolones and ethenesulfonyl fluoride was achieved, providing a portal to a class of unique cyclobutane-fused pyridinyl sulfonyl fluorides with quaternary rigid rings (30 examples). Further applications of these novel sulfonyl fluoride molecules in SuFEx click chemistry were also accomplished, providing the corresponding sulfonates and sulphonamides with reasonable yields.
- Liu, Jing,Wang, Shi-Meng,Qin, Hua-Li
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supporting information
p. 4019 - 4023
(2020/06/09)
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- N - And O -arylation of pyridin-2-ones with diaryliodonium salts: Base-dependent orthogonal selectivity under metal-free conditions
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Metal-free N- and O-arylation reactions of pyridin-2-ones as ambident nucleophiles have been achieved with diaryliodonium salts on the basis of base-dependent chemoselectivity. In the presence of N,N-diethylaniline in fluorobenzene, pyridin-2-ones were very selectively converted to N-arylated products in high yields. On the other hand, the O-arylation reactions smoothly proceeded with the use of quinoline in chlorobenzene, leading to high yields and selectivities. In these methods, a variety of pyridin-2-ones in addition to pyridin-4-one and a set of diaryliodonium salts were accepted as suitable reaction partners.
- Abe, Yusuke,Hanazawa, Natsumi,Katagiri, Kotone,Kuriyama, Masami,Ono, Shimpei,Onomura, Osamu,Yamamoto, Kosuke
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p. 8295 - 8300
(2020/09/09)
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- Iron-Catalyzed Reactions of 2-Pyridone Derivatives: 1,6-Addition and Formal Ring Opening/Cross Coupling
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In the presence of simple iron salts, 2-pyridone derivatives react with Grignard reagents under mild conditions to give the corresponding 1,6-addition products; if the reaction medium is supplemented with an aprotic dipolar cosolvent after the actual addition step, the intermediates primarily formed succumb to ring opening, giving rise to non-thermodynamic Z,E-configured dienoic acid amide derivatives which are difficult to make otherwise. Control experiments as well as the isolation and crystallographic characterization of a (tricarbonyl)iron pyridone complex suggest that the active iron catalyst generated in situ exhibits high affinity to the polarized diene system embedded into the heterocyclic ring system of the substrates, which likely serves as the actual recognition element.
- Huang, Lin,Gu, Yiting,Fürstner, Alois
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supporting information
p. 4017 - 4023
(2019/08/07)
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- Metal-free regioselective direct thiolation of 2-pyridones
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A highly regioselective metal-free direct C-H thiolation of 2-pyridones with disulfides or thiols has been developed. A combination of persulfate and a commercially available halide source such as LiCl, NCS or I2 enables the successful direct incorporation of a sulfide moiety into the 5-position of pyridone under mild conditions, providing a useful and convenient approach for the preparation of a diverse array of 5-thio-substituted pyridones in moderate to excellent yields.
- Phakdeeyothin, Kunita,Yotphan, Sirilata
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supporting information
p. 6432 - 6440
(2019/07/09)
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- Substituent Effects of 2-Pyridones on Selective O-Arylation with Diaryliodonium Salts: Synthesis of 2-Aryloxypyridines under Transition-Metal-Free Conditions
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An efficient transition-metal-free strategy to synthesize 2-aryloxypyridine derivatives has been developed by a selective O-arylation of 2-pyridones with diaryliodonium salts. The reaction was compatible with a series of functional groups for 2-pyridones and diaryliodonium salts such as halides, nitro, cyano, and ester groups. The substituents at the C6-position of 2-pyridones favored O-arylation products because of steric hindrance. The reaction was easily performed on a gram-scale and 6-chloro-2-pyridone was a good precursor to access various unsubstituted 2-aryloxypyridines by dehalogenation. A P2Y 1 lead compound analogue could be prepared in good yield over two steps.
- Li, Xiao-Hua,Ye, Ai-Hui,Liang, Cui,Mo, Dong-Liang
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p. 1699 - 1710
(2018/02/06)
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- N-Arylpyridiniophosphines: Synthesis, Structure, and Applications in Au(I) Catalysis
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The synthesis and characterization through NMR and X-ray crystallography of a series of N-arylpyridiniophosphines and their corresponding Au(I)-derivatives are reported. Because of their acceptor properties, pyridiniophosphines efficiently enhance the ele
- Tinnermann, Hendrik,Nicholls, Leo D. M.,Johannsen, Tim,Wille, Christian,Golz, Christopher,Goddard, Richard,Alcarazo, Manuel
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p. 10457 - 10463
(2018/10/24)
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- Copper(I)-USY as a Ligand-Free and Recyclable Catalyst for Ullmann-Type O-, N-, S-, and C-Arylation Reactions: Scope and Application to Total Synthesis
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The copper(I)-doped zeolite CuI-USY proved to be a versatile, efficient, and recyclable catalyst for various Ullmann-type coupling reactions. Easy to prepare and cheap, this catalytic material enables the arylation and heteroarylation of diverse O-, N-, S-, and C-nucleophiles under ligand-free conditions while exhibiting large functional group compatibility. The facility of this catalyst to promote C-O bond formation was further demonstrated with the total synthesis of 3-methylobovatol, a naturally occurring diaryl ether of biological relevance. From a mechanistic viewpoint, two competitive pathways depending on the nature of the nucleophile and consistent with the obtained results have been proposed.
- Garnier, Tony,Danel, Mathieu,Magné, Valentin,Pujol, Anthony,Bénéteau, Valérie,Pale, Patrick,Chassaing, Stefan
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p. 6408 - 6422
(2018/05/31)
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- C(sp2)-H Trifluoromethylation of enamides using TMSCF3: Access to trifluoromethylated isoindolinones, isoquinolinones, 2-pyridinones and other heterocycles
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A method for the direct C(sp2)-H trifluoromethylation of enamides, including biologically relevant isoindolinones, isoquinolinones and 2-pyridinones using TMSCF3 under oxidative conditions is presented. The protocol is convenient, operationally simple and exhibits high tolerance across a multitude of relevant handles and functional groups.
- Krishnamurti, Vinayak,Munoz, Socrates B.,Ispizua-Rodriguez, Xanath,Vickerman, Jeffrey,Mathew, Thomas,Surya Prakash
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supporting information
p. 10574 - 10577
(2018/09/27)
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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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- A highly efficient Suzuki-Miyaura methylation of pyridines leading to the drug pirfenidone and its CD3 version (SD-560)
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Efficient introduction of methyl or methyl-d3 into aromatic and heteroaromatic systems still presents a synthetic challenge. In particular, we were in search of a non-cryogenic synthesis of the 5-CD3 version of pirfenidone (4d, also known as Pirespa, Esbriet or Pirfenex), one of the two drugs approved to date for retarding idiopathic pulmonary fibrosis (IPF), a serious, rare and fatal lung disease, with a life expectancy of 3-5 years. The methyl-deuterated version of pirfenidone (4e, also known as SD-560) was designed with the objective of attenuating the rate of drug metabolism, and our goal was to find a green methylation route to avoid the environmental and economic impact of employing alkyllithium at cryogenic temperatures. The examination of several cross-coupling strategies for the introduction of methyl or methyl-d3 into methoxypyridine and pyridone systems culminated in two green and nearly quantitative Suzuki-Miyaura cross-coupling routes in the presence of RuPhos ligand: the first, using commercially available methyl boronic acid or its CD3 analog and the second, employing potassium methyl trifluoroborate or CD3BF3K, the latter obtained by a new route in 88% yield. This led, on a scale of tens of grams, to the synthesis of pirfenidone (4d) and its d3 analog, SD-560 (4e), at 99% isotopic purity.
- Falb, Eliezer,Ulanenko, Konstantin,Tor, Andrey,Gottesfeld, Ronen,Weitman, Michal,Afri, Michal,Gottlieb, Hugo,Hassner, Alfred
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supporting information
p. 5046 - 5053
(2017/11/09)
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- Deep Eutectic Solvent Compatible Metallic Catalysts: Cationic Pyridiniophosphine Ligands in Palladium Catalyzed Cross-Coupling Reactions
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Cationic pyridiniophosphine ligands have been synthetized in an attempt to develop a deep eutectic solvents (DESs) compatible catalytic systems. These ligands, in combination with PdCl2, have been successfully applied to different palladium-catalyzed cross coupling reactions, such as Suzuki–Miyaura, Sonogashira, or Heck couplings. While traditional palladium ligands in DES medium failed to reproduce the results obtained in VOC solvents, these cationic phosphines improved the catalytic activity of palladium as no other traditional ligand could in such a polar medium. In addition, the recyclability of these processes was studied, allowing us to reuse both, catalyst and solvent up to 5 times in Suzuki and Sonogashira reactions without a significant drop in the catalytic activity. Regarding the structure of the Pd catalysts, titration, NMR, and DFT studies have clearly demonstrated the coordination properties of the DES-compatible cationic phosphine ligands.
- Marset, Xavier,Khoshnood, Abbas,Sotorríos, Lia,Gómez-Bengoa, Enrique,Alonso, Diego A.,Ramón, Diego J.
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p. 1269 - 1275
(2017/04/14)
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- Rhodium(III)-Catalyzed Annulation of Pyridinones with Alkynes via Double C-H Activation: A Route to Functionalized Quinolizinones
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A Rh(III)-catalyzed oxidative annulation of pyridin-2(1H)-ones with alkynes via double C-H activation to produce highly functionalized 4H-quinolizin-4-ones is disclosed. This reaction features easily available starting materials, simple manipulation, a relatively wide substrate scope, and good functional group tolerance. The application of this protocol is demonstrated by the synthesis of a known fluorescent quinolizino[3,4,5,6-ija]quinolinium salt.
- Li, Juan,Yang, Yudong,Wang, Zhigang,Feng, Boya,You, Jingsong
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supporting information
p. 3083 - 3086
(2017/06/23)
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- Green alternative solvents for the copper-catalysed arylation of phenols and amides
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Investigation of the use of green organic solvents for the Cu-catalysed arylation of phenols and amides is reported. Alkyl acetates proved to be efficient solvents in the catalytic processes, and therefore excellent alternatives to the typical non-green solvents used for Cu-catalysed arylation reactions. Solvents such as isosorbide dimethyl ether (DMI) and diethyl carbonate also appear to be viable possibilities for the arylation of phenols. Finally, a novel copper catalysed acyl transfer process is reported.
- Sambiagio, Carlo,Munday, Rachel H.,John Blacker,Marsden, Stephen P.,McGowan, Patrick C.
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p. 70025 - 70032
(2016/08/06)
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- Synthesis, structure, and applications of pyridiniophosphines
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A new family of cationic ligands, N-alkyl/aryl pyridiniophosphines, has been synthesized through a short, scalable, and highly modular route. Evaluation of their electronic properties evidenced weak σ-donor and quite strong π-acceptor character when used
- Tinnermann, Hendrik,Wille, Christian,Alcarazo, Manuel
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p. 8732 - 8736
(2014/08/18)
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- Copper ferrite nanoparticle-mediated N-arylation of heterocycles: A ligand-free reaction
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The synergistic effects of iron and copper in copper ferrite nanoparticles for the N-arylation of heterocycles with aryl halides were demonstrated. The magnetic nature of the catalyst facilitates its removal from the reaction medium for further use. Negligible leaching of Cu and Fe in consecutive cycles makes the catalyst economical and environmentally benign for C-N cross-coupling reactions.
- Panda, Niranjan,Jena, Ashis Kumar,Mohapatra, Sasmita,Rout, Smruti Ranjan
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supporting information; experimental part
p. 1924 - 1927
(2011/04/25)
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- COMPOUNDS AND METHODS FOR TREATING INFLAMMATORY AND FIBROTIC DISORDERS
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Disclosed are compounds and methods for treating inflammatory and fibrotic disorders, including methods of modulating a stress activated protein kinase (SAPK) system with an active compound, wherein the active compound exhibits low potency for inhibition of the p38 MAPK; and wherein the contacting is conducted at a SAPK-modulating concentration that is at a low percentage inhibitory concentration for inhibition of the p38 MAPK by the compound. Also disclosed are derivatives and analogs of pirfenidone, useful for modulating a stress activated protein kinase (SAPK) system.
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Page/Page column 87
(2009/12/28)
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- Copper-catalyzed N-arylation of amides and azoles using phosphine-free hydrazone ligands
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Phosphine-free hydrazone such as 1c was found to be an efficient ligand for the copper-catalyzed Goldberg-type N-arylation of amides and Ullmann-type N-arylation of azoles with aryl halides under mild conditions. A variety of N-arylamides and N-arylazoles were synthesized in good to high yields. Georg Thieme Verlag Stuttgart.
- Mino, Takashi,Harada, Yoshikazu,Shindo, Hiroaki,Sakamoto, Masami,Fujita, Tsutomu
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p. 614 - 620
(2008/12/22)
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- A β-keto ester as a novel, efficient, and versatile ligand for copper(I)-catalyzed C-N, C-O, and C-S coupling reactions
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(Formula Presented) Employing ethyl 2-oxocyclohexanecarboxylate as a novel, efficient, and versatile ligand, the copper-catalyzed coupling reactions of various N/O/S nucleophilic reagents with aryl halides could be successfully carried out under mild conditions. A variety of products including N-arylamides, N-arylimidazoles, aryl ethers, and aryl thioethers were synthesized in good to excellent yields.
- Lv, Xin,Bao, Weiliang
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p. 3863 - 3867
(2008/02/02)
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- N-arylation of pyridin-2(1H)-ones with pentavalent organobismuth reagents under copper-free conditions
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An efficient method for the N-arylation of pyridin-2(1H)-ones and the related heteroaromatic lactams has been established via ligand-coupling reactions using tri- or tetra-aryl organobismuth(V) reagents such as triarylbismuth dichlorides. Also, N-alkenylation of pyridin-2(1H)-one was achieved similarly by using alkenyltriarylbismuth(V) reagents.
- Ikegai, Kazuhiro,Nagata, Yuzo,Mukaiyama, Teruaki
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p. 761 - 767
(2008/02/01)
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- Method of forming a carbon-carbon or carbon-heteroatom linkage
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The invention relates to a method of creating a carbon-carbon or carbon-heteroatom linkage by reacting an unsaturated compound bearing a leaving group and a nucleophilic compound. More specifically, the invention relates to the creation of a carbon-nitrogen linkage involving the arylation of nitrogenous organic derivatives. The inventive method consists in creating a carbon-carbon or carbon-heteroatom linkage by reacting an unsaturated compound bearing a leaving group and a nucleophilic compound providing a carbon atom or a heteroatom (HE) capable of being substituted for the leaving group, thereby creating a C—C or C-HE linkage. The invention is characterised in that the reaction is carried out in the presence of an effective quantity of a catalyst based on copper and at least one ligand comprising at least one imine function and at least one additional nitrogen atom as chelating atoms
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Page/Page column 32-33
(2010/02/14)
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- An improved Ullmann-Ukita-Buchwald-Li conditions for CuI-catalyzed coupling reaction of 2-pyridones with aryl halides
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An effective CuI-trans-N,N′-dimethylcyclohexane-1,2-diamine (DMCDA)-K2CO3-catalyzed coupling reaction of 2-pyridones with aryl halides is described. Under our conditions, DMCDA was found to be an effective catalyst that facilitates the coupling reactions even in toluene, a common industrial solvent. In addition, 3-bromopyridine could also be coupled effectively under these conditions, indicating that the catalytic reactivity of this system is high. The reaction could be applied for polymer modification and iterative oligo-pyridone synthesis.
- Wang, Po-Shih,Liang, Chih-Kai,Leung, Man-Kit
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p. 2931 - 2939
(2007/10/03)
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- TOPICAL ANTISEPTIC COMPOSITIONS AND METHODS
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In a preferred embodiment, a method of treating bacteria, fungi, and/or viruses on the surface of, or within, the layers of the dermis of skin, ears, fingernails, toenails, or hoofs of mammalian species, comprising: applying to the surface or layers a pharmaceutical substance including an effective amount of one or more 2-(1H) pyridone compound(s).
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- Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides
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Mild, efficient, copper-catalyzed N-arylation procedures for nitrogen heterocycles, amides, carbamates, and C-arylation procedures for malonic acid derivatives have been developed that afford high yields of arylated products with excellent selectivity. The N-arylation of imidazole with aryl bromides or iodides was found to be greatly accelerated by inexpensive, air-stable catalyst systems, combining catalytic copper salts or oxides with a set of structurally simple chelating ligands. The reaction was shown to be compatible with a broad range of aryl halides, encompassing sterically hindered, electron-poor, and electron-rich ones, providing the arylated products under particularly mild conditions (50-82°C). The lower limit in ligand and catalyst loading and the scope of Ullmann-type condensations catalyzed by complexes bearing those ligands with respect to the nucleophile class have also been investigated. Chelating Schiff base Chxn-Py-Al (1c) generates a remarkably general copper catalyst for N-arylation of pyrrole, indole, 1,2,4-triazole, amides, and carbamates; and C-arylation of diethyl malonate, ethyl cyanoacetate, and malononitrile with aryl iodides under mild conditions (50-82°C). The new method reported here is the most successful to date with regard to Ullmann-type arylation of some of these nucleophiles.
- Cristau, Henri-Jean,Cellier, Pascal P.,Spindler, Jean-Francis,Taillefer, Marc
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p. 5607 - 5622
(2007/10/03)
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- Process for arylating or vinylating or alkynating a nucleophilic compound
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The present invention concerns a process for arylating or vinylating or alkynating a nucleophilic compound. More particularly, the invention concerns arylating nitrogen-containing organic derivatives. The arylating or vinylating or alkynating process of the invention consists of reacting a nucleophilic compound with a compound carrying a leaving group and is characterized in that the reaction is carried out in the presence of an effective quantity of a catalyst based on a metallic element M selected from groups (VIII), (Ib) and (IIb) of the periodic table and at least one ligand comprising at least one imine function and at least one supplemental nitrogen atom as the chelating atoms.
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- Copper-promoted C-N bond cross-coupling with phenylstannane
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Copper-promoted C-N bond cross-coupling of NH-containing substrates with phenylstannane at room temperature was accomplished with the addition of TBAF.
- Lam, Patrick Y.S.,Vincent, Guillaume,Bonne, Damien,Clark, Charles G.
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p. 3091 - 3094
(2007/10/03)
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- Cyclic ureas as ortho directing substituents
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Six-membered cyclic ureas are shown to have a weak ortho directing ability when linked through nitrogen to benzene and pyridine rings.
- Meigh,Alvarez,Joule
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p. 2012 - 2021
(2007/10/03)
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- Treatment of cytokine growth factor caused disorders
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In preferred embodiments, a method of prevention and treatment of disorders caused by enhanced proliferation and enhanced biosynthesis caused by cytokine growth factors in humans and other animals, the method including: administering to a human or other animal an effective dose of a pharmaceutical substance including an N-substituted 2(1H) pyridone and/or an N-substituted 3(1H) pyridone; and a composition for prevention and treatment of disorders caused by enhanced proliferation and enhanced biosynthesis caused by cytokine growth factors in humans and other animals, the composition including: a pharmaceutical preparation including an effective dose of an N-substituted 2(1H) pyridone and/or an N-substituted 3(1H) pyridone.
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- Compositions and method for treatment of lymphomas, leukemias, and leiomyomas
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In a preferred embodiment, drugs having chemotherapeutic properties which are useful against certain neoplastic disorders with wide safety margins as evidenced by their low toxicity, and molecular actions. Such drugs include as active ingredient(s) one or more N-substituted 2-(1H) pyridone(s) and/or N-substituted 3-(1H) pyridone(s). The compositions of this invention are novel as anti-neoplastic drugs, namely as an agent for treating leukemias, lymphomas, and leiomyomas.
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- Inhibition of tumor necrosis factor α
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In a preferred embodiment, a method for the inhibition of the synthesis and release of tumor necrosis factor from various cells, comprising: administering to a human or other mammal an effective dose of one or more pharmaceutical substances selected from the group consisting of N-substituted 2(1H)pyridones, N-substituted 3(1H)pyridones, and pharmaceutically acceptable salts thereof.
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- Compositions and methods for reparation and prevention of fibrotic lesions
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In a preferred embodiment, drugs having pharmacological properties which are useful in the medicinal therapy of fibrotic disease for the reparation and prevention of fibrotic lesional tissues, such drugs including as active ingredient(s) one or more N-substituted 2-(1H) pyridone(s) and/or N-substituted 3-(1H) pyridones. The composition of this invention is novel as an anti-fibrotic drug, namely, as an agent for treating fibrosis. Any existing compounds have not been shown to be effective for the reparation and prevention of fibrotic lesions.
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- A facile copper-catalyzed Ullmann condensation: N-arylation of heterocyclic compounds containing an -NHCO- moiety
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N-Aryl heterocyclic compounds were synthesized from aryl halides and heterocyclic compounds containing an -NHCO- moiety by using a catalytic amount (1-10 mol%) of a commercially available copper catalyst in satisfactory yields. This catalytic reaction was applicable to the synthesis of N-aryl-2-pyridone, -2-pyrrolidone, -1(2H)-isoquinolone, -1(2H)- phthalazinone, -4(3H)-quinazolinone and -1,2,3-benzotriazin-4(3H)-one derivatives.
- Sugahara, Masakatsu,Ukita, Tatsuzo
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p. 719 - 721
(2007/10/03)
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- Compositions and methods for reparation and prevention of fibrotic lesions
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In a preferred embodiment, drugs having pharmacological properties which are useful in the medicinal therapy of fibrotic disease for the reparation and prevention of fibrotic lesional tissues, such drugs including as the active ingredient one or more N-substituted 2-(1H) pyridone(s). The composition of this invention is novel as an anti-fibrotic drug, namely, as an agent for treating fibrosis. Any existing compounds have not been shown to be effective for the reparation and prevention of fibrotic lesions.
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- The Structure-Reactivity-Chemoselectivity Relationship on the Reactions of 1-Unsubstituted Tautomeric 2-Pyridones with Benzyne
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The reactions of 2-pyridones with benzyne were investigated in order to gain some insight into the structure-reactivity-chemoselectivity relatinoship involved in the tautomeric systems.All reactions examined have resulted in the formation of Diels-Alder and Michael-type adducts.It has been shown that the Diels-Alder reactivities were well correlated with the HOMO energy levels of the 2-pyridone form and the yields of the Michael-type adduct were closely associated with the tautomeric equilibria.In summary, the chemoselectivities of 2-pyridones in the reaction with benzyne were largely affected by the tautomeric properties.
- Kuzuya, Masayuki,Noguchi, Akihiro,Mano, Ei-ichi,Okuda, Takachiyo
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p. 1149 - 1155
(2007/10/02)
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- Direkte N-Arylierung von Amiden: Eine Verbesserung der Goldberg-Reaktion
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The copper-catalyzed N-arylation of amides, the Goldberg reaction, usually requires drastic reaction conditions and produces only moderate yields of the desired products.Much better results can be achieved by modifying the reaction conditions.We used copper on silica as a catalyst and potassium acetate as a base and continuously removed the resulting acetic acid from the reaction mixture.In this way we gained high, in some cases nearly quantitative yields of the arylated or heteroarylated products.
- Renger, Bernd
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p. 856 - 860
(2007/10/02)
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- 5-Methyl-1-phenyl-2-(1H)-pyridone compositions and methods of use
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Novel analgesic, anti-pyretic, anti-inflammatory compositions containing as the active ingredient the compound, 5-methyl-1-phenyl-2-(1H)-pyridone are described. Such compositions have also been found to cause significant lowering of serum uric acid and glucose levels and to be effective in the treatment of a number of upper respiratory ailments in humans and other mammals. Skin conditions such as dermatitis and poison ivy are also alleviated by this agent. The compositions containing 5-methyl-1-phenyl-2-(1H)-pyridone caused no irritation on oral administration or when applied to specific target tissues showed no significant irritation or other sequelae.
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