- A convenient and practical heterogeneous palladium-catalyzed carbonylative Suzuki coupling of aryl iodides with formic acid as carbon monoxide source
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A practical heterogeneous palladium-catalyzed carbonylative Suzuki coupling of aryl iodides with arylboronic acids under carbon monoxide gas-free conditions has been developed using a bidentate phosphino-functionalized magnetic nanoparticle-immobilized palladium(II) complex as catalyst. Formic acid was utilized as the carbon monoxide source with dicyclohexylcarbodiimide as the activator, and a wide variety of biaryl ketones were generated in moderate to high yields. The new heterogeneous palladium catalyst can be prepared via a simple procedure and can easily be separated from a reaction mixture by simply applying an external magnet and recycled up to 10 times without any loss of activity.
- You, Shengyong,Yan, Chenyu,Zhang, Rongli,Cai, Mingzhong
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Read Online
- From Pyridine- N-oxides to 2-Functionalized Pyridines through Pyridyl Phosphonium Salts: An Umpolung Strategy
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The reactions of pyridine-N-oxides with Ph3P under the developed conditions provide an unprecedented route to (pyridine-2-yl)phosphonium salts. Upon activation with DABCO, these salts readily serve as functionalized 2-pyridyl nucleophile equivalents. This umpolung strategy allows for the selective C2 functionalization of the pyridine ring with electrophiles, avoiding the generation and use of unstable organometallic reagents. The protocol operates at ambient temperature and tolerates sensitive functional groups, enabling the synthesis of otherwise challenging compounds.
- Bugaenko, Dmitry I.,Yurovskaya, Marina A.,Karchava, Alexander V.
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supporting information
p. 6099 - 6104
(2021/08/03)
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- Copper(i)-catalyzed tandem synthesis of 2-acylquinolines from 2-ethynylanilines and glyoxals
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An efficient one-step synthesis of 2-acylquinolines using a copper-catalyzed tandem reaction of 2-ethynylanilines with glyoxals in the presence of piperidine has been developed. This new protocol successfully avoids multi-step operation and the use of highly toxic cyanides required in traditional methods, and provides a practical tool for synthetic and pharmaceutical chemists. Various 2-acylquinolines are obtained with perfect regioselectivity in moderate to good yields (up to 86%). The potential synthetic utility of this method is exemplified by a large-scale experiment and synthetic transformation of the products.
- Chu, Xiaoxiao,Jia, Jian,Liu, Gang,Liu, Xiguang,Wang, Guanghui,Yu, Mingwu,Zhao, Ximei
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supporting information
p. 11811 - 11814
(2021/11/30)
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- K2S2O8activation by glucose at room temperature for the synthesis and functionalization of heterocycles in water
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While persulfate activation at room temperature using glucose has primarily been focused on kinetic studies of the sulfate radical anion, the utilization of this protocol in organic synthesis is rarely demonstrated. We reinvestigated selected K2S2O8-mediated known organic reactions that invariably require higher temperatures and an organic solvent. A diverse, mild functionalization and synthesis of heterocycles using the inexpensive oxidant K2S2O8 in water at room temperature is reported, demonstrating the sustainability and broad scope of the method. Unlike traditional methods used for persulfate activation, the current method uses naturally abundant glucose as a K2S2O8 activator, avoiding the use of higher temperature, UV light, transition metals or bases.
- Hunjan, Mandeep Kaur,Laha, Joydev K.
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p. 8437 - 8440
(2021/09/02)
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- Minisci aroylation of N-heterocycles using choline persulfate in water under mild conditions
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Metal persulfate mediated thermal oxidative organic transformations invariably require a higher temperature and frequently use an organic solvent. The objective of this work was to develop persulfate mediated oxidative transformations that can be performed nearly at room temperature using water as a solvent. This report describes modified Minisci aroylation of isoquinolines with arylglyoxylic acids using choline persulfate and its pre-composition (choline acetate and K2S2O8) in water at 40 °C. A few other nitrogen heterocycles were also utilized affording various aroylated products in good to excellent yields. Unlike metal persulfate that could produce metal salt byproducts, a key feature of the chemistry reported herein includes the use of environmentally benign choline persulfate containing biodegradable choline as a counter-cation, the Minisci reaction demonstrated at 40 °C in water as the only solvent, and unconventional activation of persulfate. This journal is
- Hunjan, Mandeep Kaur,Laha, Joydev K.,Tinwala, Ummehani
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p. 22853 - 22859
(2021/12/24)
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- Synthesis method of 2-aroyl quinoline derivative
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The invention relates to a synthesis method of a 2-aroyl quinoline derivative, which comprises the following steps: by taking 2-bromoaniline and aryl cyclobutanol as reaction substrates, palladium chloride as a catalyst, tricyclohexylphosphine as a ligand, cesium carbonate as alkali and ultra-dry toluene as a solvent, stirring and reacting for 12 hours under the protection of nitrogen at 110 DEG C, then taking tetrabutylammonium iodide as a phase transfer catalyst, under the conditions of acetic acid and potassium persulfate, stirring and reacting for 16 hours at 90 DEG C by taking methylbenzene as a solvent; the method has the advantages of relatively low requirements on reaction conditions, mild conditions, simple operation steps, simple and easily available raw materials, great reduction of environmental pollution and the like.
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Paragraph 0011
(2021/11/19)
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- Photo-redox catalyzed dehydrazinative acylation of N-heterocycles: Via Minisci reaction
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Visible light-induced acylation of heteroaromatic compounds have been achieved using benzoyl hydrazides as an efficient acyl source under mild reaction conditions. The photo-redox catalyzed oxidative cleavage of hydrazides leads to in situ formation of ac
- Hafeez, Saira,Saeed, Aamer
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p. 38683 - 38689
(2021/12/20)
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- Preparation method of 2-quinolylphenyl ketone compound
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The invention discloses a preparation method of a 2-quinolylphenyl ketone compound. According to the preparation method, 2-acetenyl aniline, phenyl glyoxal and piperidine are used as initial raw materials, and are subjected to a gold-catalyzed three-component coupling reaction (A3 couplings) and an intramolecular condensation reaction so as to synthesize the 2-quinolylphenyl ketone in one step. The preparation method has the advantages of cheap and easily available raw materials, simple operation steps, mild reaction conditions, high atom economy and excellent regioselectivity, and meets the needs of large-scale industrial production. The prepared 2-quinolylphenyl ketone is an important active drug molecule and can be used as a cannabinoid CB2 receptor stimulant.
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Paragraph 0031-0035
(2021/11/10)
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- Photoenzymatic Hydrogenation of Heteroaromatic Olefins Using ‘Ene’-Reductases with Photoredox Catalysts
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Flavin-dependent ‘ene’-reductases (EREDs) are highly selective catalysts for the asymmetric reduction of activated alkenes. This function is, however, limited to enones, enoates, and nitroalkenes using the native hydride transfer mechanism. Here we demonstrate that EREDs can reduce vinyl pyridines when irradiated with visible light in the presence of a photoredox catalyst. Experimental evidence suggests the reaction proceeds via a radical mechanism where the vinyl pyridine is reduced to the corresponding neutral benzylic radical in solution. DFT calculations reveal this radical to be “dynamically stable”, suggesting it is sufficiently long-lived to diffuse into the enzyme active site for stereoselective hydrogen atom transfer. This reduction mechanism is distinct from the native one, highlighting the opportunity to expand the synthetic capabilities of existing enzyme platforms by exploiting new mechanistic models.
- Biegasiewicz, Kyle F.,Black, Michael J.,Chung, Megan M.,Hyster, Todd K.,Meichan, Andrew J.,Nakano, Yuji,Sandoval, Braddock A.,Zhu, Tianyu
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p. 10484 - 10488
(2020/04/29)
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- Rhodium-Catalyzed Pyridine N-Oxide Assisted Suzuki-Miyaura Coupling Reaction via C(O)-C Bond Activation
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A rhodium-catalyzed Suzuki-Miyaura coupling reaction via C(O)-C bond activation to form 2-benzoylpyridine N-oxide derivatives is reported. Both the C(O)-C(sp2) and C(O)-C(sp3) bond could be activated during the reaction with yields up to 92%. The N-oxide moiety could be employed as a traceless directing group, leading to free pyridine ketones.
- Zhong, Jing,Long, Yang,Yan, Xufei,He, Shiyu,Ye, Runyou,Xiang, Haifeng,Zhou, Xiangge
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supporting information
p. 9790 - 9794
(2019/12/24)
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- RuII-Catalyzed/NH2-Assisted Selective Alkenyl C-H [5 + 1] Annulation of Alkenylanilines with Sulfoxonium Ylides to Quinolines
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A novel ruthenium-catalyzed [5 + 1] annulation of 2-alkenylanilines with sulfoxonium ylides was developed for the rapid assembly of highly functionalized quinolines. This new catalytic process employs challenging but synthetically ideal free amino functionality to achieve alkenyl C-H activation with sulfoxonium ylides as one-carbon coupling partners. Various 2-acylquinolines could be obtained with good yields and excellent functional group tolerance. Moreover, the potential synthetic application of this methodology was exemplified by several chemical transformations.
- Chen, Pu,Nan, Jiang,Hu, Yan,Ma, Qiong,Ma, Yangmin
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supporting information
p. 4812 - 4815
(2019/06/27)
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- Photoredox-Catalyzed Decarboxylative C-H Acylation of Heteroarenes
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A mild, environmentally friendly, and regioselective acylation of heterocycles with inexpensive carboxylic acids is reported via photoredox catalysis. The strategy is highlighted with good functional group tolerance and substrate scope which could rapidly
- Jia, Wei,Jian, Yong,Huang, Binbin,Yang, Chao,Xia, Wujiong
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supporting information
p. 1881 - 1886
(2018/08/28)
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- Synthesis method of acylated quinoline or isoquinoline derivative
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The invention discloses a synthesis method of an acylated quinoline or isoquinoline derivative, belongs to the field of organic synthesis, and aims to solve the problems of complicated reaction, severe conditions and low environmental friendliness in the
- -
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Paragraph 0045-0049
(2019/07/29)
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- Acyl Radicals from Terminal Alkynes: Photoredox-Catalyzed Acylation of Heteroarenes
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A photoredox-mediated acylation reaction of electron deficient heteroarenes with terminal alkynes is reported. The method relies on oxidative cleavage of phenylacetylenes for generation of acyl radicals as a key enabling feature. The reaction is regiosele
- Sultan, Shaista,Rizvi, Masood Ahmad,Kumar, Jaswant,Shah, Bhahwal Ali
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supporting information
p. 10617 - 10620
(2018/07/31)
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- Room Temperature Metal-Catalyzed Oxidative Acylation of Electron-Deficient Heteroarenes with Alkynes, Its Mechanism, and Application Studies
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Herein, we report an original one-step, simple, room-temperature, regioselective Minisci reaction for the acylation of electron-deficient heteroarenes with alkynes. The method has broad functional group compatibility and gives exclusively monoacylated products in good to excellent yields. The mechanistic pathway was analyzed based on a series of experiments confirming the involvement of a radical pathway. The 18O-labeling experiment suggested that water is a source of oxygen in the acylated product, and head space GC-MS experiment shows the C-C cleavage occurs via release as CO2.
- Sharma, Shweta,Kumar, Mukesh,Vishwakarma, Ram A.,Verma, Mahendra K.,Singh, Parvinder Pal
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p. 12420 - 12431
(2018/10/20)
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- Copper-Catalyzed Aerobic Oxygenation of Benzylpyridine N-Oxides and Subsequent Post-Functionalization
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A copper-catalyzed aerobic oxidation of benzylpyridine N-oxides is reported. The N-oxide moiety acts as a built-in activator for the benzylic methylene oxidation, without requirement of additives. Reaction conditions were identified which suppress undesired benzoylpyridine formation via N-deoxygenation involving intermolecular oxygen transfer. The versatility of the N-oxide group of the benzoylpyridine N-oxide reaction products for post-functionalization of the pyridine ring is demonstrated through efficient C–C, C–N, C–O and C–Cl bond forming procedures, with both nucleophiles and electrophiles. Finally, the applicability of the new synthetic methodology is demonstrated in an alternative route towards the antihistaminic drug Acrivastine via three consecutive N-oxide activated C–H functionalization processes, starting from picoline N-oxide. (Figure presented.).
- Sterckx, Hans,Sambiagio, Carlo,Médran-Navarrete, Vincent,Maes, Bert U. W.
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supporting information
p. 3226 - 3236
(2017/09/13)
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- Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen
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The methylene group of various substituted 2- and 4-benzylpyridines, benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthesis is exemplified by the alternative synthesis of a precursor to the antimalarial drug Mefloquine. The oxidation method can also be used to prepare metabolites of APIs which is illustrated for the natural product papaverine. ICP-MS analysis of the purified reaction products revealed that the base metal impurity was well below the regulatory limit.
- Sterckx, Hans,De Houwer, Johan,Mensch, Carl,Herrebout, Wouter,Tehrani, Kourosch Abbaspour,Maes, Bert U.W.
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supporting information
p. 144 - 153
(2016/04/05)
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- Benzylation of heterocyclic N-oxides via direct oxidative cross-dehydrogenative coupling with toluene derivatives
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A novel cross-dehydrogenative coupling (CDC) of heterocyclic N-oxides with toluene derivatives has been discussed, allowing for the facile synthesis of a broad range of structurally diverse C1-benzyl quinoline N-oxides, isoquinoline N-oxides and pyridine N-oxides, including two methylated quinoline N-oxides in particular. This protocol not only extends the application of toluenes in synthetic organic chemistry, but also offers an alternative method to prepare benzylated heterocyclic N-oxides without any metal involved, which is important in medicinal chemistry.
- Wan,Qiao,Sun,Di,Fang,Li,Guo
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p. 10227 - 10232
(2016/12/07)
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- Transition-Metal-Free Acylation of Quinolines and Isoquinolines with Arylmethanols via Oxidative Cross-Dehydrogenative Coupling Reactions
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An efficient acylation of quinolines and isoquinolines is described by use of arylmethanols as the acylating agents through a C-C bond formation via an oxidative cross-dehydrogenative coupling (CDC) strategy. This C-aroylation reaction was carried out by use of K2S2O8 as oxidant and methyltrioctylammonium chloride (Aliquat 336) as a transfer agent in MeCN at 80 °C under transition-metal-free conditions.
- Adib, Mehdi,Pashazadeh, Rahim,Rajai-Daryasarei, Saideh,Kabiri, Roya,Gohari, Seyed Jamal Addin
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supporting information
p. 2241 - 2245
(2016/10/11)
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- TBHP/TFA mediated oxidative cross-dehydrogenative coupling of N-heterocycles with aldehydes
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An effective and metal-free oxidative cross-dehydrogenative coupling (CDC) of N-heterocycles with diverse aldehydes has been established in the presence of TBHP/TFA. The scope with respect to aldehyde and N-heterocycle components is broad, allowing facile synthesis of a broad range of structurally diverse C1-acyl substituted heterocycles in good efficiency.
- Chen, Jiayu,Wan, Miao,Hua, Jing,Sun, Yi,Lv, Zheng,Li, Wei,Liu, Lei
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p. 11561 - 11566
(2015/12/04)
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- Regiospecific benzoylation of electron-deficient n -heterocycles with methylbenzenes via a minisci-type reaction
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A regioselective cross-dehydrogenative coupling between electron-deficient N-heterocycles (isoquinoline, quinolines, and quinoxalines) and methylbenzenes leading to regiospecific C-aroylation has been accomplished using AlCl3 as the catalyst in
- Ali, Wajid,Behera, Ahalya,Guin, Srimanta,Patel, Bhisma K.
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p. 5625 - 5632
(2015/06/16)
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- Copper-catalyzed oxidative amination of sp3 C-h bonds under air: Synthesis of 1,3-diarylated imidazo[1,5-a ]pyridines
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A copper(II)-catalyzed tandem reaction between pyridine ketone and benzylamine was developed by using clean O2 as an oxidant. This transformation proceeded via an efficient condensation-amination-oxidative dehydrogenation process, affording 1,3-diarylated imidazo[1,5-a]pyridines in excellent yields.
- Wang, Huiqiao,Xu, Wentao,Wang, Zhiqiang,Yu, Lintao,Xu, Kun
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p. 2431 - 2435
(2015/04/14)
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- Organocatalytic C-H bond arylation of aldehydes to bis-heteroaryl ketones
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An organocatalytic aldehyde C-H bond arylation process for the synthesis of complex heteroaryl ketones has been developed. By exploiting the inherent electrophilicity of diaryliodonium salts, we have found that a commercial N-heterocyclic carbene catalyst promotes the union of heteroaryl aldehydes and these heteroaromatic electrophile equivalents in good yields. This straightforward catalytic protocol offers access to ketones bearing a diverse array of arene and heteroarene substituents that can subsequently be converted into molecules displaying structural motifs commonly found in medicinal agents.
- Toh, Qiao Yan,McNally, Andrew,Vera, Silvia,Erdmann, Nico,Gaunt, Matthew J.
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supporting information
p. 3772 - 3775
(2013/04/24)
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- Oxidation of secondary benzylic alcohols to ketones and benzylic oxygenation of alkylarenes with hydrogen peroxide in the presence of activated carbon
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A variety of benzylic alcohols were oxidized to the corresponding carbonyl compounds selectively with 30% hydrogen peroxide (H in the presence of activated carbon. Alkylarenes such as fluorenes, xanthenes, and anthrone were also effectively oxygenated to the corresponding carbonyl compounds with 30% Has oxidant in the presence of activated carbon. Georg Thieme Verlag Stuttgart · New York.
- Nishida, Shunsuke,Hayashi, Masahiko
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experimental part
p. 1683 - 1685
(2012/08/13)
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- A general access to 1,1-cyclopropane aminoketones and their conversion into 2-benzoyl quinolines
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1,1-Cyclopropane aminoketones were efficiently synthesized in high yields by the tandem reaction of α-amino aryl ketones with vinyl sulfonium salts using DBU as the base in CH2Cl2. This methodology was utilized to synthesize 2-benzoyl quinolines. The Royal Society of Chemistry 2012.
- Mao, Zhenjun,Qu, Haijun,Zhao, Yanyan,Lin, Xufeng
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supporting information
p. 9927 - 9929
(2012/11/06)
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- Synthesis of quinolinyl and isoquinolinyl phenyl ketones as novel agonists for the cannabinoid CB2 receptor
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A series of quinolinyl and isoquinolinyl phenyl ketones was synthesized and their CB2 receptor-dependent G-protein activities were determined using the [35S]GTPγS binding assay. Both quinoline and isoquinoline derivatives exhibited similar CB2 receptor agonist activity, the most potent ligands being the 2-(Me2N)-phenyl substituted derivatives, which were also full agonists at the CB2-receptor.
- Reux, Bastien,Nevalainen, Tapio,Raitio, Katri H.,Koskinen, Ari M.P.
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experimental part
p. 4441 - 4447
(2009/11/30)
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- Oxidation of secondary benzylic alcohols to ketones by activated carbon-molecular oxygen system
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A variety of benzylic alcohols were oxidized to the corresponding carbonyl compounds selectively in the presence of activated carbon under molecular oxygen atmosphere. This process does not require any metal oxides, thus this is environmentally friendly and economical. Copyright
- Sano, Yuki,Tanaka, Takanori,Hayashi, Masahiko
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p. 1414 - 1415
(2008/03/14)
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- Acetonitrile Derivatives as Carbonyl Synthons. One-Pot Preparation of Diheteroaryl Ketones via a Strategy of Sequential SNAr Substitution and Oxidation
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The anion of 2-aryl acetonitrile derivatives reacted with a variety of heteroaryl chlorides or bromides in an SNAr manifold to afford intermediate anions which were susceptible to oxidation. The addition of sodium peroxide and aqueous NH4OAc solution effected oxidation to afford aryl heteroaryl ketones in good yields. Aryl acetonitrile derivatives are thus umpolung-type synthons of the corresponding aryl carbonyl functionality.
- Yin, Zhiwei,Zhang, Zhongxing,Kadow, John F.,Meanwell, Nicholas A.,Wang, Tao
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p. 1364 - 1367
(2007/10/03)
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- Polar effects in free-radical reactions. A novel homolytic acylation of heteroaromatic bases by aerobic oxidation of aldehydes, catalysed by N-hydroxyphthalimide and Co salts
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A new process for the homolytic acylation of protonated heteroaromatic bases is described; an N-oxyl radical (PINO) generated from N-hydroxyphthalimide by air oxygen and Co(II) abstracts a hydrogen atom from an aldehyde. The resulting nucleophilic acyl radical adds to a heteroaromatic base, which is then rearomatised in a chain process. Quinazoline has an anomalous behaviour, giving 3H-quinazolin-4-one as the only reaction product.
- Minisci, Francesco,Recupero, Francesco,Cecchetto, Andrea,Punta, Carlo,Gambarotti, Cristian,Fontana, Francesca,Pedulli, Gian Franco
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p. 325 - 328
(2007/10/03)
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- Naphthalene-catalysed lithiation of chlorinated nitrogenated aromatic heterocycles and reaction with electrophiles
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Naphthalene catalysed reductive lithiation of various chloroazines (1, 7, 10, 13) in the presence of different electrophiles yields, after hydrolysis, the expected functionalised heterocycles with one (2, 8), two (11, 14a-d) and three nitrogen atoms in the ring (14e,f). This methodology allowed us to trap in situ the lithium imine derived from the reaction of 2- pyridyllithium with benzonitrile, by reaction with a Grignard reagent in the presence of titanium alkoxides. 2,4-Dimethoxypyrimidines (14a,c,d) are demethylated under acidic conditions to give the corresponding uracil derivatives 16. (C) 2000 Elsevier Science Ltd.
- Gómez, Inmaculada,Alonso, Emma,Ramón, Diego J.,Yus, Miguel
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p. 4043 - 4052
(2007/10/03)
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- Simple and mild method for preparation of α-pyridinecarboxylates and α-pyridyl ketones via trimethylstannyl derivatives
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Alkoxycarbonylation and acylation at the α-position of pyridine, quinoline, and isoquinoline via the respective trimethylstannyl derivatives were satisfactorily performed by employing ethyl chloroglyoxylate and acylformyl chloride under mild conditions.
- Yamamoto,Ouchi,Tanaka
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p. 1028 - 1030
(2007/10/03)
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- ELECTROPHILIC REACTION OF PYRIDINE, QUINOLINE, ISOQUINOLINE, THEIR N-OXIDES AND THEIR BORON TRIFLUORIDE COMPLEXES THROUGH BASE-INDUCED DEPROTONATION
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The comparative studies have been carried out on reactivities of pyridine, quinoline, isoquinoline, and their BF3 complexes, their N-oxides, and their N-oxide-BF3-complexes, towards the electrophilic reaction through α-deprotonation.
- Tagawa, Yoshinobu,Hama, Kazuya,Goto, Yoshinobu,Hamana, Masatomo
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p. 809 - 816
(2007/10/02)
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- ELECTROPHILIC REACTION OF QUINOLINE 1-OXIDE THROUGH BASE-INDUCED DEPROTONATION
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Lithiation of quinoline 1-oxide-BF3 complex (3) with LTMP and TMEDA in ether at -78 deg C followed treatment with benzaldehyde or cyclohexanone affords the corresponding 2-substituted derivatives (4,5 or 6), while the reaction of quinoline 1-oxide (1) itself under the same conditions results ih the formation of 2,2'-biquinoline 1-oxide (2).
- Tagawa, Yoshinobu,Hama, Kazuya,Goto, Yoshinobu,Hamana, Masatomo
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p. 2243 - 2246
(2007/10/02)
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- Homolytic Acylation of Protonated Pyridines and Pyrazines with α-Keto Acids: The Problem of Monoacylation
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The silver-catalyzed decarboxylation of α-keto acids by persulfate leads to acyl radicals, which can effect the selective homolytic acylation of pyridine and pyrazine derivatives.Compared with the previously developed source of acyl radicals by hydrogen abstraction from aldehydes, this procedure is more effective in monoacylation when multiple positions of high nucleophilic reactivity are available in the heterocyclic ring.Although the introduction of an acyl group strongly activates the heterocyclic ring toward further substitution, monoacylation can be achieved by taking advantage of the difference in basicity and lipophilicity between the starting base and the monoacylation products in a two-phase system.
- Fontana, Francesca,Minisci, Francesco,Barbosa, Maria Claudia Nogueira,Vismara, Elena
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p. 2866 - 2869
(2007/10/02)
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- Synthesis and Chromogenic Properties of Some Water-Soluble 5-Nitro-2-pyridylhydrazones
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Four new water-soluble hydrazones, α-(5-nitro-2-pyridyl)hydrazono-α-(2-quinolyl)-3-toluenesulfonic acid, α-(5-nitro-2-pyridyl)hydrazono-α-(2-thiazolyl)-3-toluenesulfonic acid, α-(2-benzothiazolyl)-α-(5-nitro-2-pyridyl)hydrazono-3-toluenesulfonic acid, and α-(2-benzimidazolyl)-α-(5-nitro-2-pyridyl)hydrazono-3-toluenesulfonic acid, were synthesized.Their proton dissociation constants were determined spectrophotometrically.The chromogenic properties of the synthesized hydrazones and their reactions with metal ions were investigated spectrophotometrically in detail.The results revealed that the synthesized hydrazones react with various metal ions including transition metal ions, especially with cadmium(II), nickel(II), and zinc(II) to form stable colored comoplexes with very large apparent molar absorptivities, so that their were found to be all very useful as highly sensitive spectrophotometric reagents.
- Ishi, Hajime,Odashima, Tsugikatsu,Kawamonzen, Yoshiaki,Katahira, Aoba-ku,Odashima, Tsugikatsu
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p. 3398 - 3404
(2007/10/02)
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- REACTION OF METHOXY-N-HETEROAROMATICS WITH PHENYLACETONITRILE UNDER BASIC CONDITIONS
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The monomethoxyl derivatives of various ?-electron deficient N-heteroaromatics reacted with phenylacetonitrile in tetrahydrofuran in the presence of sodium hydride to give α-phenyl-N-heteroareneacetonitriles in the yields ranging from 45 to 78percent.On the contrary, the reaction of these methoxyl derivatives with ethyl cyanoacetate or malononitrile under similar conditions was restricted within narrow limits.The synthesis of benzoyl-N-heteroaromatics by the air-oxidation of α-phenyl-N-hetroareneacetonitriles was described additionally.
- Yamanaka, Hiroshi,Ohba, Setsuya
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p. 895 - 909
(2007/10/02)
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- Sels de N-alcoxyquinoleinium et d'isoquinoleinium porteurs d'une fonction cetone dans leur chaine alcoxyle: synthese et reactivite vis-a-vis d'amines secondaires
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Reaction of α-bromoisobutyrophenone on quinoline 1-oxide and isoquinoline 2-oxide in the presence of silver perchlorate leads to N-alkoxyquinolinium and isoquinolinium salts bearing a keto group in their alkoxyl chain.On treatment with secondary amines these salts are quantitatively converted to 2-benzoylquinoline and 1-benzoylisoquinoline.This conversion results from a decomposition analogous to the Katritzky mode A of the intermediate isoxazoloquinolinium or isoquinolinium salts which are first formed by a Proton Abstraction Ring Closure sequence.These tricyclic intermediates have been isolated when 2,2,6,6-tetramethylpiperidine was used.
- Sliwa, Henry,Ouattara, Lassina
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p. 1617 - 1620
(2007/10/02)
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- A NEW ACCESS TO 2-BENZOYLQUINOLINE AND 1-BENZOYLISOQUINOLINE USING A NOVEL MODE OF BASE-INDUCED DECOMPOSITION OF N-ALKOXYPYRIDINIUM SALTS
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A novel mode of fragmentation alkoxylogous of Katritzky's mode A of decomposition of N-alkoxypyridinium salts can become exclusive in the quinoline and isoquinoline series, providing a new access to benzoyl derivatives of these heterocycles.
- Sliwa, Henri,Ouattara, Lassina
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p. 3065 - 3069
(2007/10/02)
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- A New Synthesis of Aryl Hetaryl Ketones via SRN1 Reaction of Halogenated Heterocycles withPotassiophenylacetonitrile Followed by Phase-Transfer Catalyzed Decyanation
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Reaction of halogenated pyridines, quinolines, pyrimidines, and pyrazines with potassiophenylacetonitrile (5) in liquid ammonia under near-uv irradiation affords secondary nitriles, which then undergo oxidative decyanation under phase-transfer catalytic conditions to afford aryl hetaryl ketones in excellent yields.
- Hermann, Christine K. F.,Sachdeva, Yesh P.,Wolfe, James F.
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p. 1061 - 1065
(2007/10/02)
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- Studies on Tertiary Amine Oxides. LXXX.1) Reaction of Quinoline 1-oxide with Phenylacetic Anhydride
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Treatment of quinoline 1-oxide (1) with phenylacetic acid and acetic anhydride in boiling benzene for 10 h gave benzaldehyde (2), quinoline (3), 2-benzylquinoline (4), 2-benzoylquinoline (5), phenyl-di(2-quinolyl)carbinol (6), di(2-quinolyl) ketone (7), and N-(2-quinolyl)-2-benzylidene-1,2-dihydroquinoline (8) in small yields.The reaction of 1 with phenylacetic anhydride in boiling benzene for 10 h afforded 1,3-diphenyl-1-(2-quinolyl)acetone (9) and dibenzyl ketone (10) together with small amounts of 2, 3, and 5.Further, it was found that phenylacetic anhydrideundergoes decarboxylative coupling upon heating with tertiary amines to give 10.The mechamisms of these reactions are discussed. Keywords --- nucleophilic reaction; oxidative decarboxylation; decarboxylative coupling; benzaldehyde; 2-benzylquinoline; phenyl-di(2-quinolyl)carbinol; N-(2-quinolyl)-2-benzylidene-1,2-dihydroquinoline; 1,3-diphenyl-1-(2-quinolyl)acetone; dibenzyl ketone
- Funakoshi, Kazuhisa,Mizuoka, Masae,Wada, Kazuko,Saeki, Seitaro,Hamana, Masatomo
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p. 3886 - 3891
(2007/10/02)
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- Studies on Organometallic Compounds. III. Reaction of Trimethylstannylazines with Acyl Chlorides. A Novel C-C Bond Formation of Pyridine Nuclei
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Introduction of an acyl group at the α-, β-, and γ-positions of pyridine nuclei was accomplished. 2-Trimethylstannyl-pyridine and -quinoline and 1-trimethylstannylisoquinoline directly reacted with various acyl chlorides to give the corresponding 2-pyridyl, 2-quinolyl, and 1-isoquinolyl ketones, respectively.Reaction of 3-trimethylstannylpyridine, -quinoline, and -isoquinoline with acyl chlorides proceeded smoothly under catalysis by PdCl2 or PdCl2(PPh3)2 to afford the corresponding ketones in good yields.Similary, 4-pyridyl, -quinolyl, and -isoquinolyl ketones were prepared from corresponding 4-trimethylstannyl derivatives and acyl chlorides.Keywords--trimethylstannylazine; palladium-catalyzed reaction; acylation; palladium dichloride; dichlorobis(triphenylphosphine)palladium(II)
- Yamamoto, Yutaka,Yanagi, Akihiko
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p. 2003 - 2010
(2007/10/02)
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- A SIMPLE METHOD FOR INTRODUCTION OF ACYL GROUPS INTO PYRIDINE NUCLEI VIA TRIMETHYLSTANNYL-PYRIDINES AND QUINOLINES.
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The 2-trimethylstannyl (TMSn) derivatives of pyridine and quinoline were directly treated with acyl chlorides to afford the corresponding 2-acyl-pyridines and -quinolines in good yields.On the other hand, replacement of the 3- and 4-TMSn groups by acyl groups was satisfactorily achieved by catalysis of palladium compound such as PdCl2 or PdCl2(PPh3)2.
- Yamamoto, Yutaka,Yanagi, Akihiko
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