- 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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- ZnMe2-Mediated, Direct Alkylation of Electron-Deficient N-Heteroarenes with 1,1-Diborylalkanes: Scope and Mechanism
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The regioselective, direct alkylation of electron-deficient N-heteroarenes is, in principle, a powerful and efficient way of accessing alkylated N-heteroarenes that are important core structures of many biologically active compounds and pharmaceutical agents. Herein, we report a ZnMe2-promoted, direct C2- or C4-selective primary and secondary alkylation of pyridines and quinolines using 1,1-diborylalkanes as alkylation sources. While substituted pyridines and quinolines exclusively afford C2-alkylated products, simple pyridine delivers C4-alkylated pyridine with excellent regioselectivity. The reaction scope is remarkably broad, and a range of C2- or C4-alkylated electron-deficient N-heteroarenes are obtained in good yields. Experimental and computational mechanistic studies imply that ZnMe2 serves not only as an activator of 1,1-diborylalkanes to generate (α-borylalkyl)methylalkoxy zincate, which acts as a Lewis acid to bind to the nitrogen atom of the heterocycles and controls the regioselectivity, but also as an oxidant for rearomatizing the dihydro-N-heteroarene intermediates to release the product.
- Jo, Woohyun,Baek, Seung-Yeol,Hwang, Chiwon,Heo, Joon,Baik, Mu-Hyun,Cho, Seung Hwan
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supporting information
p. 13235 - 13245
(2020/09/01)
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- One-Pot Oxidative Synthesis of Substituted Quinolines from Alcohols and Arylamines Catalyzed by Fe(CrO2)2 in Water Medium
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One-pot tandem synthesis was developed for substituted quinolines (in up to 97% yields) involving a selective catalytic oxidation of primary amines to aldehydes and their condensation with arylamines under the action of a dispersion of Fe(CrO2)2 and water solution of H2O2 at room temperature. The stage of catalytic oxidation of alcohols was accelerated by photoactivation. A presumable mechanism of the photoactivated tandem synthesis of 2-methylquinoline was suggested. Catalyst Fe(CrO2)2 was prepared by photochemical synthesis.
- Makhmutov
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p. 1166 - 1172
(2018/10/24)
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- Fe(CrO2)2-catalyzed, photoactivated oxidative one-pot tandem synthesis of substituted quinolines from primary alcohols and arylamines
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[Figure not available: see fulltext.] A one-pot tandem synthesis of substituted quinolines involving selective catalytic oxidation of primary alcohols to the corresponding aldehydes and their subsequent condensation with arylamines has been developed. Fe(CrO2)2 has been used as a catalyst, and oxidation has been performed with aqueous H2O2. To accelerate the catalytic oxidation of alcohols, photoactivation method has been applied.
- Makhmutov, Aynur R.,Mustafin, Akhat G.,Usmanov, Salavat M.
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p. 369 - 374
(2018/05/28)
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- Sequential Photoredox Catalysis for Cascade Aerobic Decarboxylative Povarov and Oxidative Dehydrogenation Reactions of N-Aryl α-Amino Acids
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A visible-light-driven sequential photoredox catalysis to allow N-aryl α-amino acids to experience efficient cascade aerobic decarboxylative Povarov and oxidative dehydrogenation (ODH) reactions is described. With a dicyanopyrazine-derived chromophore (DP
- Shao, Tianju,Yin, Yanli,Lee, Richmond,Zhao, Xiaowei,Chai, Guobi,Jiang, Zhiyong
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supporting information
p. 1754 - 1760
(2018/03/21)
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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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- 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 0081; 0082
(2017/06/02)
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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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- Quinoline Synthesis by the Reaction of Anilines with 1,2-diols Catalyzed by Iron Compounds
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The synthesis of quinoline derivatives by cyclocondensation of anilines with 1,2-ethanediol, 1,2-propanediol, and 1,2-butanediol in the presence of iron-containing catalysts was performed for the first time.
- Khusnutdinov, Ravil,Bayguzina, Alfiya,Aminov, Rishat,Dzhemilev, Usein
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supporting information
p. 1022 - 1029
(2016/07/28)
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- Quinolines synthesis by reacting 1,3-butanediol with anilines in the presence of iron catalysts
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2-, 4-, 6-, 7-, and 8-substituted quinolines were synthesized in 78–95% yield by the reaction of 1,3- butanediol with anilines in the presence of iron catalysts in carbon tetrachloride.
- Khusnutdinov,Bayguzina,Aminov
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p. 1613 - 1618
(2016/08/26)
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- PYRAZOLOPYRIDINE PYRAZOLOPYRIMIDINE AND RELATED COMPOUNDS
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In one aspect this invention relates generally to compounds of Formula: and sub-formulas thereof, or a tautomer of each thereof, a pharmaceutically acceptable salt of each thereof, or a pharmaceutically acceptable solvate of each of the foregoing, where X1, L1, L3, and R3 are described herein.
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Paragraph 1518; 1519
(2015/11/25)
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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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- Synthesis of substituted quinolines by the reaction of anilines with alcohols and CCl4 in the presence of Fe-containing catalysts
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Substituted quinolines were synthesized by the reaction of aniline derivatives with aliphatic alcohols and CCl4 upon the action of the FeCl3·6H2O catalyst.
- Khusnutdinov,Bayguzina,Aminov
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p. 133 - 137
(2013/11/19)
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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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- Arenesulfonic acid-functionalized mesoporous silica decorated with titania: A heterogeneous catalyst for the one-pot photocatalytic synthesis of quinolines from nitroaromatic compounds and alcohols
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Acid-modified mesoporous SiO2 decorated with TiO2 (T-S-ArSO3H) was successfully prepared via the co-condensation of 2-(4-chlorosulfonylphenyl)ethyltrimethoxysilane (CSPTMS) and tetraethyl orthosilicate in the presence of commercially available Sachtleben Hombikat UV100 TiO2 particles. The resulting bifunctional catalyst induced the efficient one-pot photocatalytic conversion of nitroaromatic compounds into polyalkylated quinolines in O2-free alcoholic solutions. In this process, a simultaneous reduction of the nitro compound and an oxidation of the alcohol are induced by the photogenerated electrons and holes, respectively. An imine is then produced upon condensation of the generated aldehyde and amino compounds. The cyclization of the produced imine yielding polyalkylated quinoline was found to be catalyzed by the surface attached arene-SO 3H group. The newly synthesized catalyst was characterized by TEM and BET measurements, by FTIR, TGA, as well as by an acid-base titration method.
- Hakki, Amer,Dillert, Ralf,Bahnemann, Detlef W.
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p. 565 - 572
(2013/05/09)
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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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- One-pot photocatalytic synthesis of quinaldines from nitroarenes with Au loaded TiO2 nanoparticles
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One-pot photocatalytic synthesis of quinaldines from nitroarenes using Au-TiO2 nanoparticles is reported. Au-TiO2 on irradiation induces a combined redox reaction with nitroarene and alcohol and the products undergo condensation-cyclization process to give quinaldines.
- Selvam,Swaminathan
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scheme or table
p. 389 - 393
(2011/12/15)
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- Novel redox photocatalyst Pt-TiO2 for the synthesis of 2-Methylquinolines from nitroarenes
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An eco-friendly and efficient procedure for synthesis of 2-methylquinoline derivatives from nitroarenes has been developed by a simple one-pot reaction on the surface of platinum-loaded TiO2 with neat ethanol under UV irradiation without any harsh reagent according to green chemistry. TiO 2 catalysts with various amounts of Pt loadings were prepared by photodeposition using chloroplatinic acid solution and characterized by XRD, BET, AFM, HR-TEM, XPS, and DRS. XRD patterns showed that the crystal structure of Pt-TiO2 still remained as anatase phase. The UV-vis spectra indicated that Pt promoted the absorption of visible light. The XPS measurements reveal that platinum particles are present mainly in metallic form. AFM and HR-TEM analysis revealed the presence of nonspherical shaped platinum nanoparticles of the diameter 312 nm. Pt-TiO2 on irradiation induces a combined redox reaction with nitroarene and alcohol and this is followed by condensationcyclization of aniline and oxidation products to give 2-methylquinolines
- Selvam, Kaliyamoorthy,Swaminathan, Meenakshisundaram
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experimental part
p. 953 - 959
(2011/10/18)
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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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- Complete study of the pyrolysis and gasification of scrap tires in a pilot plant reactor
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The pyrolysis and gasification of tires was investigated in a pilot plant reactor provided with a system for condensation of semivolatile matter. The study comprised experiments at 450°, 750°, and 1000°C both in nitrogen and 10% oxygen atmospheres. In the gas phase, only methane and benzene yields increased with temperature until 1000°C. In the liquids, the main components were styrene, limonene, and isoprene. The solid fraction (including soot) increased with temperature. Zinc content of the char decreased with increasing temperature. Analysis of the surface area of the solids showed that the area was similar in all cases to that of a commercial carbon black. The higher surface of the soot with respect to the chars was observed. The results coincided with published findings, i.e., kinetic severity function values would produce 0.2% of methane at 450°C and 4.5% at 750°-1000°C.
- Conesa, Juan A.,Martin-Gullon,Font,Jauhiainen
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p. 3189 - 3194
(2008/12/21)
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- Doebner-miller synthesis in a two-phase system: Practical preparation of quinolines
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Doebner-Miller cyclization was carried out in a two-phase solvent system. The method has shown to be advantageous to the yield and to the ease of the work-up process. (C) 2000 Elsevier Science Ltd.
- Matsugi,Tabusa,Minamikawa
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p. 8523 - 8525
(2007/10/03)
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- Thermolysis of Polyazapentadienes. Part 7. An Unambiguous Route to 7-Substituted Quinolines from Cinnamaldehyde Derivatives
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Flash vacuum pyrolysis of the cinnamaldehyde phenylhydrazone derivatives (4) - (6) or O-alkyl oxime derivatives (7) - (12) at 600 -650 deg C and 10-2 - 10-3 Torr leads to approximately equal quantities of cinnamonitriles and quinolines.Use of a p-substituted cinnamaldehyde derivatives gives the appropriate 7-substituted quinoline in high isomeric purity; the reactions take place via conjugated iminyl radicals.
- Hickson, Clare L.,McNab, Hamish
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p. 1569 - 1572
(2007/10/02)
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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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