- Porous FeO(OH) Dispersed on Mg-Al Hydrotalcite Surface for One-Pot Synthesis of Quinoline Derivatives
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The use of ubiquities elements such as iron instead of expensive precious metals as catalysts is one goal toward realizing environmentally benign synthetic chemistry. Here, we report that porous FeO(OH) dispersed on Mg?Al hydrotalcite acts as a bifunctional heterogeneous catalyst in the one-pot synthesis of 2-substituted quinoline derivatives through dehydrogenative oxidation-cyclization reactions. The catalyst was prepared by a simple grafting method using FeCl3 and Mg?Al hydrotalcite. The prepared porous FeO(OH) possesses a higher surface area than those previously reported for α-FeO(OH) particles. The one-pot quinoline synthesis proceeded effectively under non-noble-metal catalysis in air without requiring additional homogeneous bases or solvents.
- Motokura, Ken,Ozawa, Nao,Sato, Risako,Manaka, Yuichi,Chun, Wang-Jae
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p. 2915 - 2921
(2021/05/27)
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- Ruthenium-catalyzed acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones to quinolines in the presence of carbonate salt
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A ruthenium complex bearing a functional 2,2′-bibenzimidazole ligand [(p-cymene)Ru(BiBzImH2)Cl][Cl] was designed, synthesized and found to be a general and highly efficient catalyst for the synthesis of quinolines via acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones in the presence of carbonate salt. It was confirmed that NH units in the ligand are crucial for catalytic activity. The application of this catalytic system for the scale-gram synthesis of biologically active molecular was also undertaken. Notably, this research exhibits new potential of metal–ligand bifuctional catalysts for acceptorless dehydrogenative reactions.
- Xu, Xiangchao,Ai, Yao,Wang, Rongzhou,Liu, Liping,Yang, Jiazhi,Li, Feng
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p. 340 - 349
(2021/02/27)
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- Mild and Robust Stille Reactions in Water using Parts Per Million Levels of a Triphenylphosphine-Based Palladacycle
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An inexpensive and new triphenylphosphine-based palladacycle has been developed as a pre-catalyst, leading to highly effective Stille cross-coupling reactions in water under mild reaction conditions. Only 500–1000 ppm of Pd suffices for couplings involving a variety of aryl/heteroaryl halides with aryl/hetaryl stannanes. Several drug intermediates can be prepared using this catalyst in aqueous nanoreactors formed by 2 wt % Brij-30 in water.
- Takale, Balaram S.,Thakore, Ruchita R.,Casotti, Gianluca,Li, Xaiohan,Gallou, Fabrice,Lipshutz, Bruce H.
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p. 4158 - 4163
(2021/02/01)
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- Mild and efficient copper-catalyzed oxidative cyclization of oximes with 2-aminobenzyl alcohols at room temperature: synthesis of polysubstituted quinolines
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A simple and efficient ligand-free Cu-catalyzed protocol for the synthesis of polysubstituted quinolinesviaoxidative cyclization of oxime acetates with 2-aminobenzyl alcohols at room temperature has been developed. The presented approach provides a new synthetic pathway leading to polysubstituted quinolines with good functional group tolerance under mild conditions. Moreover, this transformation can be applied for the preparation of quinolines on a gram scale. Oxime acetates serve as the internal oxidants in the reactions, thus making this method very attractive.
- Liu, Yan-Yun,Wei, Yang,Huang, Zhi-Hui,Liu, Yilin
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supporting information
p. 659 - 666
(2021/02/06)
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- Half-Sandwich Ruthenium Complexes for One-Pot Synthesis of Quinolines and Tetrahydroquinolines: Diverse Catalytic Activity in the Coupled Cyclization and Hydrogenation Process
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Four types of half-sandwich ruthenium complexes with an N,O-coordinate mode based on hydroxyindanone-imine ligands have been prepared in good yields. These stable ruthenium complexes exhibited high activity in the catalytic synthesis of quinolines from the reactions of amino alcohols with different types of ketones or secondary alcohols under very mild conditions. Moreover, the methodology for the direct one-pot synthesis of tetrahydroquinoline derivatives from amino alcohols and ketones has been also developed on the basis of the continuous catalytic activity of this ruthenium catalyst in the selective hydrogenation of the obtained quinoline derivatives with a low catalyst loading. The corresponding products, quinolines and tetrahydroquinoline derivatives, were afforded in good to excellent yields. The efficient and diverse catalytic activity of these ruthenium complexes suggested their potential large-scale application. All of the ruthenium complexes were characterized by various spectroscopies to confirm their structures.
- Yun, Xue-Jing,Zhu, Jing-Wei,Jin, Yan,Deng, Wei,Yao, Zi-Jian
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supporting information
p. 7841 - 7851
(2020/06/04)
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- Metal-Ligand Cooperative Approach to Achieve Dehydrogenative Functionalization of Alcohols to Quinolines and Quinazolin-4(3 H)-ones under Mild Aerobic Conditions
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A simple metal-ligand cooperative approach for the dehydrogenative functionalization of alcohols to various substituted quinolines and quinazolin-4(3H)-ones under relatively mild reaction conditions (≤90 °C) is reported. Simple and easy-to-prepare air-stable Cu(II) complexes featuring redox-active azo-aromatic scaffolds, 2-arylazo-(1,10-phenanthroline) (L1,2), are used as catalyst. A wide variety of substituted quinolines and quinazolin-4(3H)-ones were synthesized in moderate to good isolated yields via dehydrogenative coupling reactions of various inexpensive and easily available starting materials under aerobic conditions. A few control experiments and deuterium labeling studies were carried out to understand the mechanism of the dehydrogenative coupling reactions, which indicate that both copper and the coordinated azo-aromatic ligand participate in a cooperative manner during the catalytic cycle.
- Das, Siuli,Sinha, Suman,Samanta, Deepannita,Mondal, Rakesh,Chakraborty, Gargi,Branda?, Paula,Paul, Nanda D.
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p. 10160 - 10171
(2019/08/20)
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- Dehydrogenative Synthesis of Quinolines, 2-Aminoquinolines, and Quinazolines Using Singlet Diradical Ni(II)-Catalysts
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Simple, straightforward, and atom economic methods for the synthesis of quinolines, 2-aminoquinolines, and quinazolines via biomimetic dehydrogenative condensation/coupling reactions, catalyzed by well-defined inexpensive and easy to prepare singlet diradical Ni(II)-catalysts featuring two antiferromagnetically coupled singlet diradical diamine type ligands are described. Various polysubstituted quinolines, 2-aminoquinolines, and quinazolines were synthesized in moderate to good yields from different low-cost and readily accessible starting materials. Several control experiments were carried out to get insight into the reaction mechanism which shows that the nickel and the coordinated diamine ligands participate in a synergistic way during the dehydrogenation of alcohols.
- Chakraborty, Gargi,Sikari, Rina,Das, Siuli,Mondal, Rakesh,Sinha, Suman,Banerjee, Seemika,Paul, Nanda D.
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p. 2626 - 2641
(2019/02/26)
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- A nickel catalyzed acceptorless dehydrogenative approach to quinolines
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A general, efficient and environmentally benign, one-step synthesis of substituted quinoline derivatives was achieved by acceptorless dehydrogenative coupling of o-aminobenzylalcohols with ketones and secondary alcohols catalyzed by a cheap, earth abundant and easy to prepare nickel catalyst [Ni(MeTAA)], featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)). A wide variety of substituted quinolines were synthesized in high yields starting from readily available o-aminobenzylalcohols and ketones or secondary alcohols. A few controlled reactions were carried out to establish the acceptorless dehydrogenative nature of the reactions.
- Parua, Seuli,Sikari, Rina,Sinha, Suman,Das, Siuli,Chakraborty, Gargi,Paul, Nanda D.
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p. 274 - 284
(2018/01/12)
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- π-Allylpalladium Species in Micelles of FI-750-M for Sustainable and General Suzuki-Miyaura Couplings of Unactivated Quinoline Systems in Water
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General, clean, and sustainable Suzuki-Miyaura cross-couplings of 2-and 4-quinoline and isoquinoline systems have been demonstrated with use of π-allyl Pd catalyst in the nanomicelles of environmentally benign, proline-derived surfactant FI-750-M. Optimiz
- Handa, Sachin,Ibrahim, Faisal,Ansari, Tharique N.,Gallou, Fabrice
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p. 4229 - 4233
(2018/09/21)
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- Palladium-catalyzed synthesis of quinolines from allyl alcohols and anilines
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A process for quinoline synthesis through palladium-catalyzed oxidative cyclization of aryl allyl alcohols and anilines is described. This process works in the absence of acid, base and any other additive and has a broad substrate scope, tolerating electron-withdrawing groups such as nitryl, trifluoromethyl and so on. A series of quinolines are prepared in satisfactory yields.
- Xu, Jingxiu,Sun, Jing,Zhao, Jinwu,Huang, Bin,Li, Xiaohan,Sun, Yulun
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p. 36242 - 36245
(2017/08/02)
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- Palladium-Catalyzed Allylic C-H Oxidative Annulation for Assembly of Functionalized 2-Substituted Quinoline Derivatives
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An efficient and practical palladium-catalyzed aerobic oxidative approach to afford functionalized 2-substituted quinolines in moderate to good yields from readily available allylbenzenes with aniline is developed. The present annulation process has high functional-group tolerance and high atom economy, making it a valuable and practical method in synthetic and medicinal chemistry. Moreover, this transformation is supposed to proceed through oxidation of allylic C-H functionalization to form C-C and C-N bonds in one pot.
- Li, Chunsheng,Li, Jianxiao,An, Yanni,Peng, Jianwen,Wu, Wanqing,Jiang, Huanfeng
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p. 12189 - 12196
(2016/12/23)
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- Convergent synthesis of 2-aryl-substituted quinolines by gold-catalyzed cascade reaction
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Gold-catalyzed auto-tandem catalysis has been developed for synthesizing 2-aryl-substituted quinolines. The reaction of an aniline bearing an acetal moiety with an aryl alkyne proceeded via formal [4+2]-cycloaddition, which involved the addition of gold acetylide to an oxonium ion to give amino alkyne intermediate and sequential 6-endo-dig cyclization of amino alkyne intermediate by attacking of nitrogen to alkyne moiety activated by gold catalyst. The cationic gold catalyst promoted two different processes by enhancing the nucleophilicity and electrophilicity of alkyne. This convergent synthetic methodology enabled the synthesis of a variety of 2-aryl-substituted quinolines.
- Ueda, Hirofumi,Yamaguchi, Minami,Tokuyama, Hidetoshi
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p. 824 - 829
(2016/07/14)
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- Catalytic Aerobic Dehydrogenation of Nitrogen Heterocycles Using Heterogeneous Cobalt Oxide Supported on Nitrogen-Doped Carbon
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Dehydrogenation of (partially) saturated heterocycles provides an important route to heteroaromatic compounds. A heterogeneous cobalt oxide catalyst, previously employed for aerobic oxidation of alcohols and amines, is shown to be effective for aerobic dehydrogenation of various 1,2,3,4-tetrahydroquinolines to the corresponding quinolines. The reactions proceed in good yields under mild conditions. Other N-heterocycles are also successfully oxidized to their aromatic counterparts.
- Iosub, Andrei V.,Stahl, Shannon S.
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supporting information
p. 4404 - 4407
(2015/09/28)
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- Highly enantioselective spinol-derived phosphoric acid catalyzed transfer hydrogenation of diverse C=N-containing heterocycles
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A highly efficient and enantioselective hydrogenation of diversely substituted C=N-containing heterocyclic compounds such as 3-aryl-1,4-benzoxazines and 2-arylquinolines was experimentally explored by using 1,1′-spirobiindane-7,7′-diol-derived chiral phosphoric acids as the catalyst. This method provides straightforward access to the corresponding tetrahydroquinolines and dihydro-2H-1,4-benzothiazines in high yields (85-99%) with excellent enantioselectivities (91-99%). The attractive features of this procedure, which include mild reaction conditions, operational simplicity, relatively low catalyst loading (1 mol-%), and high levels of enantioselectivities, make it a useful approach for the practical synthesis of optically active nitrogen-containing aromatic heterocycles.
- Zhang, Yiliang,Zhao, Rong,Bao, Robert Li-Yuan,Shi, Lei
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supporting information
p. 3344 - 3351
(2015/05/20)
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- Synthesis of 2-substituted quinolines from alcohols
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A facile and economic method for the construction of 2-substituted quinolines by AgOTf-catalyzed 2-aminobenzyl alcohol and alkyne/ketone or 2-aminophenethyl alcohol and aldehyde has been developed. The electronic properties of the substituents on the alkyne, ketone, and aldehyde were investigated. It was found that molecules with both electron-donating and -withdrawing substituents were perfectly suitable substrates for this transformation, and the expected products were obtained in moderate to excellent yields. Moreover, the use of inexpensive starting materials and environmentally benign oxidants makes this atom efficient method particularly attractive.
- Xu, Xuefeng,Zhang, Xu,Liu, Wenming,Zhao, Qiang,Wang, Zhiqiang,Yu, Lintao,Shi, Fu
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supporting information
p. 3790 - 3792
(2015/06/08)
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- An efficient synthesis of quinolines via copper-catalyzed C-N cleavage
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An efficient method to synthesize substituted quinolines from ketones and 2-amino benzylamines is described. Copper-catalyzed C-N cleavage of amines followed by condensation with ketones deliver quinolines in moderate to high yields. The broad scope of su
- Xi, Long-Yi,Zhang, Ruo-Yi,Zhang, Lei,Chen, Shan-Yong,Yu, Xiao-Qi
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p. 3924 - 3930
(2015/03/30)
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- Bronsted acid-mediated reactions of aldehydes with 2-vinylaniline and biphenyl-2-amine
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Herein we report simple Bronsted acid-mediated reactions of aldehydes with 2-vinylaniline and biphenyl-2-amine. Ultimately, the useful nitrogen-containing heterocycle derivatives are obtained. The electronic properties of the substituents on the aldehydes and 2-vinylaniline were investigated. It was found that molecules with both electron-donating and -withdrawing substituents were perfectly suitable substrates for this transformation, and the expected products were obtained in moderate to excellent yields.
- Zhang, Xu,Xu, Xuefeng,Yu, Lintao,Zhao, Qiang
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supporting information
p. 2280 - 2282
(2014/04/17)
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- Synthesis of substituted quinoline via copper-catalyzed one-pot cascade reactions of 2-bromobenzaldehydes with aryl methyl ketones and aqueous ammonia
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In this Letter, a new version of the Friedl?nder synthesis of quinoline derivatives starting from 2-bromobenzaldehydes, aryl methyl ketones, and aqueous ammonia with copper-catalyzed amination as a key step is presented. Remarkable advantages of this new quinoline synthesis include commercially available and economical starting materials, simple operational process, and excellent efficiency.
- Li, Bin,Guo, Chenhao,Fan, Xuesen,Zhang, Ju,Zhang, Xinying
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supporting information
p. 5944 - 5948
(2015/01/08)
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- Ferrocene-appended anionic N-heterocyclic carbene and its complex with silver(I): Synthesis, structure and catalytic evaluation
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A binuclear Ag(I) complex (1) bridged by two anionic N-heterocyclic carbene (NHC) ligands ferrocenoyl(1-mesitylimidazol- 2-ylidine-3-yl)amide is synthesized. X-ray structure reveals a [Ag...Ag] core spanned by two ligands, each bridging two metals through carbene carbon and amido nitrogen. The neutral complex (1) is highly soluble in a variety of organic solvents and is thermally stable. Complex (1) efficiently catalyses aniline-mediated synthesis of substituted quinolines from 2-aminobenzaldehyde and terminal alkynes.
- Sarbajna, Abir,Sadhukhan, Nabanita,Saha, Sayantani,Bera, Jitendra K
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p. 1072 - 1077
(2013/09/12)
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- Palladium-catalyzed sequential formation of C-C bonds: Efficient assembly of 2-substituted and 2,3-disubstituted quinolines
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A series of substituted quinolines was prepared from arylamines, aldehydes, and terminal olefins (see scheme). The palladium-catalyzed sequential formation of C-C bonds proceeds smoothly with both electron-deficient and electron-rich olefins. When acrylic acid is used as terminal olefin, decarboxylation occurs to provide 2-substituted quinolines. Copyright
- Ji, Xiaochen,Huang, Huawen,Li, Yibiao,Chen, Huoji,Jiang, Huanfeng
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supporting information; experimental part
p. 7292 - 7296
(2012/08/28)
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- Carbon-boron bond cross-coupling reaction catalyzed by -PPh2 containing palladium-indolylphosphine complexes
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This study describes the application of indolylphosphine ligands with a diphenylphosphino moiety to the palladium-catalyzed borylation of aryl chlorides. The combination of palladium metal precursor with PPh 2-Andole-phos, which comprises an inexpensive -PPh2 group, provides highly effective catalysts for the borylation of aryl chlorides. A range of functional groups such as -CN, -NO2, -CHO, -COMe, -COOMe, and -CF3 was compatible, and the catalyst loading down to 0.025 mol % of Pd can be achieved. The Pd/PPh2-Andole-phos system is able to catalyze both borylation reaction and Suzuki-Miyaura coupling reaction in a one-pot sequential manner for the direct synthesis of biaryl compounds in excellent yields.
- Chow, Wing Kin,Yuen, On Ying,So, Chau Ming,Wong, Wing Tak,Kwong, Fuk Yee
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experimental part
p. 3543 - 3548
(2012/06/15)
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- Unexpected and divergent reactions of N -formyl-1,2-dihydroquinolines with sodium azide: Highly chemoselective formation of 2-substituted quinolines and isoxazolo[4,3- c ]quinolines
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Efficient and divergent synthesis of 2-substituted quinolines and isoxazolo[4,3-c]quinolines was achieved from N-formyl-1,2-dihydroquinolines with the aid of sodium azide. The synthesis is substituent-dependent. Thus N-formyl-1,2-dihydroquinolines with a hydrogen atom at the 3-position afforded 2-substituted quinolines in good to excellent yields, while with a 3-formyl group, N-formyl-1,2-dihydroquinolines unexpectedly gave isoxazolo[4,3-c] quinolines in high yields. Georg Thieme Verlag Stuttgart.
- Su, Weike,Yu, Jingbo,Li, Zhenhua,Zheng, Bei
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supporting information; experimental part
p. 1281 - 1284
(2010/07/03)
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- Synthesis of quinolines by a solid acid-catalyzed microwave-assisted domino cyclization-aromatization approach
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A microwave-assisted solid acid-catalyzed synthesis of quinolines from anilines and cinnamaldehydes is described. Use of montmorillonite K-10 results in a one-pot process; the cyclization and oxidation steps readily take place in a domino approach. Reactions were completed in a matter of minutes and provided excellent yields. The efficient and ecofriendly catalyst and the convenience of the product isolation make this process an attractive alternative for the synthesis of these important heterocycles.
- De Paolis, Omar,Teixeira, Liliana,T?r?k, Béla
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experimental part
p. 2939 - 2942
(2009/07/26)
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- Multifunctional catalysis of a ruthenium-grafted hydrotalcite: One-pot synthesis of quinolines from 2-aminobenzyl alcohol and various carbonyl compounds via aerobic oxidation and aldol reaction
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The Ru-grafted hydrotalcite was found to be an excellent multifunctional catalyst for one-pot synthesis of quinolines from 2-aminobenzyl alcohol and various carbonyl compounds. These quinolines were obtained through aerobic oxidation by the Ru species, followed by aldol reaction on base sites of the hydrotalcite.
- Motokura, Ken,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi
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p. 6029 - 6032
(2007/10/03)
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- Ruthenium-catalysed oxidative cyclisation of 2-aminobenzyl alcohol with ketones: modified Friedlaender quinoline synthesis
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2-Aminobenzyl alcohol is oxidatively cyclised with an array of ketones in dioxane at 80 deg C in the presence of a catalytic amount of a ruthenium catalyst and KOH to afford the corresponding quinolines in high yields.
- Cho, Chan Sik,Kim, Bok Tae,Kim, Tae-Jeong,Shim, Sang Chul
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p. 2576 - 2577
(2007/10/03)
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- Substituted quinoline derivatives and pharmaceutical compositions thereof
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The novel class of substituted quinolines represented by the general formula (I): STR1 where each of R1 and R2 separately represents H or up to three of the groups lower alkyl, halogen, CF3, CN, SO2 CH3, NO2, OH, NH2, NHSO2 R3, NHCOOR3, OR3, SR3, NHR3 or NR3 R3 (where R3 is lower alkyl optionally substituted with hydroxy, amino or ether functions), and each of R1 and R2 may additionally separately represent the substitution of an aza (--N=) group for one or two of the methine (--CH=) groups in each of the carbocyclic rings, and R1 may also represent, at positions 2', 3' or 4' only, a phenyl ring optionally further substituted with lower alkyl, halogen, CF3, CN, SO2 CH3, NO2, OH, NH2, NHCOR3, NHCOOR3, OR3, SR3, NHR3 or NR3 R3 (where R3 is lower alkyl optionally substituted with hydroxy, amino or ether functions); Y represents C(NH)NH2, NHC(NH)NH2 or NR4 R5, where each of R4 and R5 is H or lower alkyl optionally substituted with hydroxy, amino or ether functions, or R4 and R5 together with the nitrogen atom form a heterocyclic ring; and n is from 2 to 6; and the acid addition salts and 1-N-oxides thereof, possess antibacterial and antitumor properties.
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