- Photocatalytic Synthesis of Quinolines via Povarov Reaction under Oxidant-Free Conditions
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We describe here an approach for synthesizing quinolines either from N-alkyl anilines or from anilines and aldehydes. A dual-catalyst system consisting of a photocatalyst and a proton reduction cocatalyst is employed. Without the use of any sacrificial ox
- Su, Long-Long,Zheng, Yi-Wen,Wang, Wen-Guang,Chen, Bin,Wei, Xiang-Zhu,Wu, Li-Zhu,Tung, Chen-Ho
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supporting information
p. 1180 - 1185
(2022/02/14)
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- Rhodium-Catalyzed C-H Annulation of Free Anilines with Vinylene Carbonate as a Bifunctional Synthon
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Chemical transformation with vinylene carbonate as an emerging synthetic unit has recently attracted considerable attention. This report is a novel conversion pattern with vinylene carbonate, in which such a vibrant reagent unprecedentedly acts as a difunctional coupling partner to complete the C-H annulation of free anilines. From commercially available substrates, this protocol leads to the rapid construction of synthetically versatile 2-methylquinoline derivatives (43 examples) with excellent functionality tolerance.
- Nan, Jiang,Yin, Jiacheng,Gong, Xue,Hu, Yan,Ma, Yangmin
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supporting information
p. 8910 - 8915
(2021/11/24)
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- Synthesis and characterization of 8-aminoquinolines, substituted by electron donating groups, as high-affinity copper chelators for the treatment of Alzheimer's disease
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The deregulation of copper homeostasis generates copper–amyloid aggregation and strongly participates in neuron damage in the brains of patients with Alzheimer's disease. Therefore, copper chelators able to regulate copper homeostasis should be considered
- Huang, Ju,Nguyen, Michel,Liu, Yan,Robert, Anne,Meunier, Bernard
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p. 419 - 427
(2019/06/13)
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- Preparation method of quinoline derivative
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The invention provides a preparation method of a quinoline derivative. The method includes the steps of: in the presence of an oxidizing agent, adding a catalyst, then adding aniline or aromatic amine with different substituents, at the same time adding alcohol for reaction so as to prepare the quinoline derivative by one step. Specifically, the catalyst comprises a metal catalyst, an assistant catalyst I and an assistant catalyst II; the metal catalyst is a transition metal catalyst; the assistant catalyst I is an alkaline nitrogen-containing ligand; and the assistant catalyst II is an acidic compound. The quinoline derivative prepared by the method provided by the invention has stable performance and high purity. And the preparation method of the quinoline derivative can prepare quinoline, 2-methylquinoline, 8-hydroxyquinoline quinoline and other derivatives by one-step reaction, and the preparation method is simple and practicable. The preparation process does not produce new "three wastes", is environment-friendly, and provides a green and environment-friendly synthesis method. The preparation method has the characteristics of few raw material variety, little reaction equipment, few preparation step and low cost, and is more suitable for industrial production.
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Paragraph 0089; 0090
(2017/06/02)
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- Assembly of Diversely Substituted Quinolines via Aerobic Oxidative Aromatization from Simple Alcohols and Anilines
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An aerobic oxidative aromatization of simple aliphatic alcohols and anilines under the Pd(OAc)2/2,4,6-Collidine/Br?nsted acid catalytic system has been established, providing a direct approach for the preparation of diverse substituted quinoline derivatives in high yields with wide functional group tolerance. Practically, the protocol can be easily scaled up to gram-scale and was utilized in the concise formal synthesis of a promising herbicide candidate.
- Li, Jixing,Zhang, Jinlong,Yang, Huameng,Jiang, Gaoxi
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supporting information
p. 3284 - 3290
(2017/03/23)
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- Blue-light-promoted carbon-carbon double bond isomerization and its application in the syntheses of quinolines
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A blue-light-promoted carbon-carbon double bond isomerization in the absence of any photoredox catalyst is reported. It provides rapid access to a series of quinolines in good to excellent yields under simple aerobic conditions. The protocol is direct, catalyst-free and operationally convenient.
- Chen, Xinzheng,Qiu, Shuxian,Wang, Sasa,Wang, Huifei,Zhai, Hongbin
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supporting information
p. 6349 - 6352
(2017/08/10)
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- Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines
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A unique, ruthenium-catalyzed, [3 + 3] annulation of anilines with allyl alcohols in the synthesis of substituted quinolines is reported. The method employs a traceless directing group strategy in the proximal C-H bond activation and represents a one-pot Domino synthesis of quinolines from anilines.
- Kumar, Gangam Srikanth,Kumar, Pravin,Kapur, Manmohan
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supporting information
p. 2494 - 2497
(2017/05/24)
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- Dual behavior of iodine species in condensation of anilines and vinyl ethers affording 2-methylquinolines
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A metal-free, mild and efficient method for the synthesis of 2-methylquinolines was successfully developed by condensation of anilines with vinyl ethers in the presence of catalytic amount of iodine. Modification of both pyridine and benzene moieties was easily achieved by changing only the vinyl ether and aniline. In this reaction, the iodine species was revealed to show dual behavior; molecular iodine serves as an oxidant, while its reduced form, hydrogen iodide, activates the vinyl ether. The redox reaction between these iodine species enables the use of a catalytic amount of iodine in this synthetic method.
- Le, Song Thi,Yasuoka, Chisa,Asahara, Haruyasu,Nishiwaki, Nagatoshi
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- Copper-Promoted Tandem Reaction of Azobenzenes with Allyl Bromides via N=N Bond Cleavage for the Regioselective Synthesis of Quinolines
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A copper-promoted tandem reaction of a variety of azobenzenes and allyl bromides via N=N bond cleavage to regioselectively construct quinoline derivatives has been developed. The azobenzenes act as not only construction units but also an oxidant for quinoline formation.
- Yi, Xiangli,Xi, Chanjuan
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supporting information
p. 5836 - 5839
(2015/12/11)
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- Magnetically separable palladium-graphene nanocomposite as heterogeneous catalyst for the synthesis of 2-alkylquinolines via one pot reaction of anilines with alkenyl ethers
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The present Letter describes the use of magnetically separable palladium-graphene nanocomposite, a complete magnetically separable catalyst for the synthesis of 2-alkyl quinolines via reaction of anilines with alkenyl ethers. Because of the uniform decoration of the Pd nanoparticles on support, the catalyst exhibited higher catalytic efficiency and it remains unaltered even after six repeated cycles.
- Verma, Sanny,Verma, Deepak,Jain, Suman L.
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p. 2406 - 2409
(2014/05/06)
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- HCV NS5A replication complex inhibitors. Part 4.1 optimization for genotype 1a replicon inhibitory activity
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A series of symmetrical E-stilbene prolinamides that originated from the library-synthesized lead 3 was studied with respect to HCV genotype 1a (G-1a) and genotype 1b (G-1b) replicon inhibition and selectivity against BVDV and cytotoxicity. SAR emerging f
- St. Laurent, Denis R.,Serrano-Wu, Michael H.,Belema, Makonen,Ding, Min,Fang, Hua,Gao, Min,Goodrich, Jason T.,Krause, Rudolph G.,Lemm, Julie A.,Liu, Mengping,Lopez, Omar D.,Nguyen, Van N.,Nower, Peter T.,O'Boyle, Donald R.,Pearce, Bradley C.,Romine, Jeffrey L.,Valera, Lourdes,Sun, Jin-Hua,Wang, Ying-Kai,Yang, Fukang,Yang, Xuejie,Meanwell, Nicholas A.,Snyder, Lawrence B.
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p. 1976 - 1994
(2014/04/03)
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- Facile synthesis of 2-methylquinolines from anilines on mesoporous N-doped TiO2 under UV and visible light
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Nitrogen-doped TiO2 was synthesized by a simple wet method using a nitrogen precursor hydrazine hydrate and nano TiO2. This photocatalyst was characterized by X-ray diffraction, highresolution transmission electron microscopy, diffused reflectance spectra, photoluminescence, and X-ray photoelectron spectroscopy. XPS analysis indicates the incorporation of anionic nitrogen in TiO2 lattice as O-Ti-N linkage. N2 adsorption-desorpion isotherm indicates the mesoporous nature of N-TiO2 with the surface area 130.0 m2/g. Sizes of N-TiO2 particles are found to be in the range of 5-30 nm by HRTEM images. DRS spectra reveal the extended absorption to the visible range. N-TiO2 is found to be more efficient than Ag-TiO2, Au-TiO2, and Pt-TiO2 in quinaldine synthesis under visible light. Copyright Taylor & Francis Group, LLC.
- Selvam,Swaminathan
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p. 500 - 508
(2013/05/21)
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- High throughput one pot synthesis of 2-methylquinolines
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Various 2-methylquinolines have been successfully synthesized by using anilines and ethyl vinyl ether in 1:3 mole ratios in the presence of acetic acid. Stirring at rt for 3-4 h followed by reflux for 3.5-4 h resulted in the corresponding 2-methylquinolines in good yield. Copyright
- Chandrashekarappa, Kiran Kumar H.,Mahadevan, Kittappa M.,Manjappa, Kiran B.
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p. 1368 - 1370
(2013/04/23)
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- Nano Pt-TiO2 for an efficient one-pot photocatalytic synthesis of quinaldines from anilines and ethanol
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Nanosized platinum particles loaded on the TiO2 nanoparticles were prepared to assess its photocatalytic activity in simple one-pot synthesis of quinaldines from anilines in ethanol using UV light. The catalyst was characterized by X-ray diffra
- Selvam, Kaliyamoorthy,Sreedhar, Bojja,Swaminathan, Meenakshisundaram
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experimental part
p. 761 - 773
(2012/08/07)
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- Assembly of substituted 2-alkylquinolines by a sequential palladium-catalyzed Ci-N and Ci-C bond formation
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Diversity: A range of substituted 2-alkylquinolines can be prepared in a general and efficient synthetic approach that employs mild reaction conditions (see scheme). The synthesis is based on a sequential palladium-catalyzed Ci-N and Ci-C bond formation, followed by palladium-catalyzed aromatization, and results in the formation of the desired compounds in one step. Copyright
- Matsubara, Yoshio,Hirakawa, Saori,Yamaguchi, Yoshihiro,Yoshida, Zen-Ichi
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experimental part
p. 7670 - 7673
(2011/10/05)
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- Au-doped TiO2 nanoparticles for selective photocatalytic synthesis of quinaldines from anilines in ethanol
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A convenient eco-friendly photocatalytic synthesis of quinaldines has been developed by a simple one-pot reaction of anilines in ethanol solution with Au-loaded TiO2 under UV irradiation. Upon irradiation in the presence of Au-TiO2, aniline and oxidation products derived from ethanol undergo condensation-cyclization to afford quinaldines.
- Selvam,Swaminathan
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scheme or table
p. 4911 - 4914
(2010/10/02)
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- Two-photon fluorescent probes of biological Zn(II) derived from 7-hydroxyquinoline
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A new fluorescent probe for monitoring Zn2+ was synthesized based on the structure of 7-hydroxyquinoline. Compared with 8-substituted quinolines, the new probe exhibited higher selectivity for Zn2+ over Cd2+. Its fluoresce
- Chen, Xiao-Yun,Shi, Jing,Li, Yi-Ming,Wang, Feng-Liang,Wu, Xu,Guo, Qing-Xiang,Liu, Lei
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supporting information; experimental part
p. 4426 - 4429
(2009/12/24)
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- Heteroannulation of 3-Bis(methylthio)acrolein with Aromatic Amines - A Convenient Highly Regioselective Synthesis of 2-(Methylthio)quinolines and their Benzo/Hetero Fused Analogs: A Modified Skraup Quinoline Synthesis
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A simple and efficient synthesis of 2-(methylthio)quinolines and their condensed analogs has been developed through acid-induced cyclocondensation of their respective anilines or aromatic diamines with 3-bis(methylthio)acrolein. The 2-(methylthio) functionality in these quinolines could be either dethiomethylated or replaced by various nitrogen and carbon nucleophiles to afford 2-substituted quinolines.
- Panda, Kausik,Siddiqui, Iffat,Mahata, Pranab K.,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
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p. 449 - 452
(2007/10/03)
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- A novel class of orally active non-peptide bradykinin B2 receptor antagonists. 3. Discovering bioisosteres of the imidazo[1,2-a]pyridine moiety
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Recently we reported on overcoming the species difference of our first orally active non-peptide bradykinin (BK) B2 receptor antagonists, incorporating an 8-[[3-(N-acylglycyl-N-methylamino)-2,6-dichlorobenzyl]oxy]- 3-halo-2-methylimidazo[1,2-α]
- Abe, Yoshito,Kayakiri, Hiroshi,Satoh, Shigeki,Inoue, Takayuki,Sawada, Yuki,Inamura, Noriaki,Asano, Masayuki,Aramori, Ichiro,Hatori, Chie,Sawai, Hiroe,Oku, Teruo,Tanaka, Hirokazu
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p. 4062 - 4079
(2007/10/03)
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- The Rhodium Complex-catalyzed Synthesis of Quinolines from Aminoarenes and Aliphatic Aldehydes
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A variety of aminoarenes react with aliphatic aldehydes in the presence of a catalytic amount of a rhodium complex and an excess amount of the corresponding nitroarenes at 180 deg C to give 2-alkyl- and 2,3-dialkyl-substituted quinolines in excellent yields.Among the rhodium complexes examined, 2 exhibits the highest activity as a catalyst.Thus, 2-methyl-, 2-ethyl-3-methyl-, 2-propyl-3-ethyl-, 2-butyl-3-propylquinoline derivatives are readily obtained from aminoarenes and ethanal, propanal, butanal, and pentanal respectively.
- Watanabe, Yoshihisa,Shim, Sang Chul,Mitsudo, Take-aki
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p. 3460 - 3465
(2007/10/02)
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