- 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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- Synthesis and SAR of cis-1-Benzoyl-1,2,3,4-tetrahydroquinoline ligands for control of gene expression in ecdysone responsive systems
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A library of 35 cis-1-benzoyl-2-methyl-4-(phenylamino)-1,2,3,4-tetrahydroquinolines was prepared. The compounds bore various substitutuents on the benzoyl ring, at the 4-position of the phenylamino ring and at the 6-position of the tetrahydroquinoline rin
- Smith, Howard C.,Cavanaugh, Caitlin K.,Friz, Jennifer L.,Thompson, Christine S.,Saggers, Jessica A.,Michelotti, Enrique L.,Garcia, Javier,Tice, Colin M.
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- Radical cation salts induced domino reaction of anilines with enol ethers: Synthesis of 1,2,3,4-tetrahydroquinoline derivatives
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A domino reaction of anilines with cyclic and acyclic enol ethers induced by catalytic amounts of TBPA?+ (5 mol%) was investigated and a series of 2,4-disubstituted-1,2,3,4-tetrahydroquinolines were synthesized. Different from cyclic enol ethers, when acyclic enol ethers were used in the reaction, they serve as surrogates of acetaldehyde, producing a series of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines. A single electron transfer mechanism was proposed to rationalize the products formation.
- Jia, Xiao Dong,Ren, Yan,Huo, Cong Dde,Wang, Wen Juan,Chen, Xiang Ning,Fu, Qiong,Wang, Xi Cun
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- 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
- Chen, Bin,Su, Long-Long,Tung, Chen-Ho,Wang, Wen-Guang,Wei, Xiang-Zhu,Wu, Li-Zhu,Zheng, Yi-Wen
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supporting information
(2022/02/14)
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- Method for synthesizing 1,2,3,4-tetrahydroquinoline compounds in mode that decarboxylation of amino acid is catalyzed by visible light
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The invention relates to a method for synthesizing 1,2,3,4-tetrahydroquinoline compounds in the mode that decarboxylation of amino acid is catalyzed by visible light. The method is characterized in that in an air atmosphere, the N-phenyl amino acidic compounds shown in the formula I, an organic photocatalyst DPZ and 4-molecular sieve are dissolved in an organic solvent, stirred and reacted for atleast 5 hours at the temperature of 20-30 DEG C under the irradiation of the visible light, separation and purification are conducted, and then the tetrahydroquinoline compounds shown in the formula II are obtained, wherein in the formula I and the formula II (the formulas are shown in the description), R is representative for any one of hydrogen, halogen, alkyl, phenyl and alkoxy, R1 is representative for any one of hydrogen, methyl, n-propyl and phenyl, alkyl is representative for methyl or ethyl or normal-butyl or benzyl, and aryl is representative for substituted phenyl or 4-tert-butyl phenyl. According to the method, substrates are simple, reaction conditions are mild, the usage amount of the catalyst is low, the yield is high, and no metal participates in a reaction.
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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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- Method for synthesizing quinoline compounds in mode that oxidative dehydrogenation of tetrahydroquinoline compounds is synergistically catalyzed by visible light
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The invention relates to a method for synthesizing quinoline compounds in the mode that oxidative dehydrogenation of tetrahydroquinoline compounds is synergistically catalyzed by visible light. The method comprises the specific steps that in an air atmosphere, the multi-substituted tetrahydroquinoline compounds shown in the formula I, an organic photocatalyst DPZ and an auxiliary catalyst Cl4-NHPIare dissolved into an organic solvent, stirred and reacted for at least 2 hours at the temperature of 20-30 DEG C under the irradiation of the visible light, separation and purification are conducted, and the quinoline compounds shown in the formula II are obtained, wherein in the formula I and the formula II (the formulas are shown in the description), R is representative for any one of hydrogen, halogen, alkyl, phenyl and alkoxy, R1 is representative for any one of hydrogen, methyl, n-propyl and phenyl, alkyl is representative for methyl or ethyl or normal-butyl or benzyl, and aryl is representative for substituted phenyl. According to the method, reaction conditions are mild, the method is environmentally friendly, the usage amount of the catalyst is low, the product conversion ratio is high, the selectivity is good and no metal participates in a reaction.
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Paragraph 0008; 0011; 0012
(2018/05/30)
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- COMPOUNDS AND MATRICES FOR USE IN BONE GROWTH AND REPAIR
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Compositions of small molecules, matrices, and isolated cells including methods of preparation, and methods for differentiation, transdifferentiation, and proliferation of animal cells into the osteoblast blast cell lineage were described. Examples of ost
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Paragraph 0333;0342;0343
(2016/03/05)
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- Efficient bromination of polyaniline base to poly(2-bromoaniline)-bromide salt and its application as a recyclable catalyst for the synthesis of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines
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Efficient bromination of polyaniline base to poly(2-bromoaniline)-bromide is successfully carried out using bromodimethylsulfonium bromide. Poly(2-bromoaniline)-bromide salt was obtained in a dry amorphous nature, having high conductivity (2.5 S/cm) with
- Rajender, Boddula,Palaniappan, Srinivasan
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- Efficient bromination of polyaniline base to poly(2-bromoaniline)-bromide salt and its application as a recyclable catalyst for the synthesis of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines
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Efficient bromination of polyaniline base to poly(2-bromoaniline)-bromide is successfully carried out using bromodimethylsulfonium bromide. Poly(2-bromoaniline)-bromide salt was obtained in a dry amorphous nature, having high conductivity (2.5 S/cm) with
- Rajender, Boddula,Palaniappan, Srinivasan
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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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supporting information; experimental part
p. 7670 - 7673
(2011/10/05)
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- Radical cation salt induced tandem cyclization between anilines and N-vinyl amides: Synthesis of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinoline derivatives
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A tandem cyclization of imines with N-vinyllactams induced by TBPA + was investigated, and a series of 2-methyl-4-anilino-1,2,3,4- tetrahydroquinolines were synthesized based on a domino process in which N-vinyllactams serve as an acetaldehyde
- Jia, Xiao-Dong,Ren, Yan,Huo, Cong-De,Wang, Wen-Juan,Chen, Xiang-Ning,Xu, Xiao-Lan,Wang, Xi-Cun
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supporting information; experimental part
p. 6779 - 6782
(2011/02/24)
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- Tetrahydroquinoline derivatives as CRTH2 antagonists
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A series of tetrahydroquinoline-derived inhibitors of the CRTH2 receptor was discovered by a high throughput screen. Optimization of these compounds for potency and pharmacokinetic properties led to the discovery of potent and orally bioavailable CRTH2 an
- Liu, Jiwen,Wang, Yingcai,Sun, Ying,Marshall, Derek,Miao, Shichang,Tonn, George,Anders, Penny,Tocker, Joel,Tang, H. Lucy,Medina, Julio
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scheme or table
p. 6840 - 6844
(2010/05/19)
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- TETRAHYDROQUINOLINES AS AGONISTS OF LIVER-RECEPTORS
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The present invention relates to specific compounds and pharmaceutically acceptable salts thereof; methods for synthesizing these compounds; compositions comprising at least one of these compounds or a pharmaceutically acceptable salt thereof; and methods
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Page/Page column 79-80
(2010/02/08)
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- Arylative amination of aldehydes promoted by aqueous titanium trichloride
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Free-radical decomposition of arene-diazonium salts 1, catalyzed by aqueous TiCl3, in the presence of aldehydes 2 and anilines 3 leads to secondary amines 4. A mechanism is proposed, according to which the aryl radical adds to the C-atom of the intermediate protonated imine.
- Clerici,Porta
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p. 2069 - 2072
(2007/10/02)
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- Catalytic and Non-catalytic Addition of Aromatic Amines to Terminal Acetylenes in the Presence of Mercury(II) Chloride and Acetate
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The addition of aromatic amines to terminal acetylenes in the presence of catalytic amounts of mercury(II) chloride gives imines, enamines, and 1,2,3,4-tetrahydroquinoline derivatives; mercury(II) acetate shows considerably less catalytic activity and may be used for the non-catalytic preparation of imines, enamines, N,N'-disubstituted acetamidines, and N,N-disubstituted acetamides.
- Barluenga, Jose,Aznar, Fernando,Liz, Ramon,Rodes, Rosa
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p. 2732 - 2737
(2007/10/02)
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