10500-57-9Relevant articles and documents
The thermodynamic properties of 1,2,3,4- and 5,6,7,8-tetrahydroquinolines
Steele, W. V.,Chirico, R. D.,Hossenlopp, I. A.,Nguyen, A.,Smith, N. K.,Gammon, B. E.
, p. 1121 - 1150 (1989)
Measurements leading to the calculation of the ideal-gas thermodynamic properties for 1,2,3,4- and 5,6,7,8-tetrahydroquinoline are reported.Thermochemical and thermophysical properties were determined by adiabatic heat-capacity calorimetry, comparative ebulliometry, inclined-piston-gauge manometry, and combustion calorimetry.Results were used to calculate standard entropies, enthalpies, and Gibbs energies of formation for the ideal-gas state at selected temperatures to 500 K.The results of the thermodynamic-property measurements were used to determine equilibrium constants, and hence, equilibrium mol alities, for the quinoline/hydrogen/tetrahydroquinoline reaction network at temperatures of interest in the processing of fossil-fuel feedstocks with a high nitrogen content.The results show that under typical processing conditions (650 K and 7.0 MPa hydrogen pressure) there is thermodynamic equilibrium between quinoline and 1,2,3,4-tetrahydroquinoline.That equilibrium conditions exist between quinoline and 5,6,7,8-tetrahydroquinoline in processing is more equivocal; however, there is strong evidence for such an equilibrium.
Reactions of 5-, 6-, 7-, 8-hydroxyquinolines and 5-hydroxyisoquinoline with benzene and cyclohexane in superacids
Koltunov, Konstantin Yu.,Prakash, G. K. Surya,Rasul, Golam,Olah, George A.
, p. 4330 - 4336 (2002)
Isomeric 5-, 6-, 7-hydroxyquinolines (11-13) and 5-hydroxyisoquinoline (14) gave N,C-diprotonated dications in CF3SO3H-SbF5 superacid medium. Compounds 11, 13, 14, and 8-hydroxyquinoline (5) underwent selective ionic hydro
Superelectrophilic activation of 8-hydroxyquinoline in acid media and its reactions with weak nucleophiles
Koltunov,Repinskaya
, p. 437 - 442 (2002)
According to the 1H and 13C NMR data, 5-azonia-4-hydroxynaphthalen-1-onium cation, generated by protonation of 8-hydroxyquinoline in the system CF3SO3H-SbF5, reacts with cyclohexane to give diprotonated 5,6,7,8-tetrahydroquinolin-8-one. Further reaction of the latter with cyclohexane yields 5,6,7,8-tetrahydroquinolinium ion. The reaction of 8-hydroxyquinoline with benzene in the presence of aluminum bromide or chloride gives 6-phenyl-5,6,7,8-tetrahydroquinolin-8-one and product of its intramolecular cyclization, 11-hydroxy-6,11-dihydro-6,11-methano-5H-benzo[5,6]cyclohepta[1,2-b]pyridine. The effect of the protonated nitrogen atom on the electrophilicity of dications is discussed.
Selective hydrogenation of N-heterocyclic compounds using Ru nanocatalysts in ionic liquids
Konnerth, Hannelore,Prechtl, Martin H. G.
, p. 2762 - 2767 (2017)
N-Heterocyclic compounds have been tested in the selective hydrogenation catalysed by small 1-3 nm sized Ru nanoparticles (NPs) embedded in various imidazolium based ionic liquids (ILs). Particularly a diol-functionalised IL shows the best performance in the hydrogenation of quinoline to 1,2,3,4-tetrahydroquinoline (1THQ) with up to 99% selectivity.
Oxidation of 1-Oxa-5-azaspiro[5.5]undecane with cyclohexanone
Kukharev,Stankevich,Klimenko,Bayandin,Kukhareva
, p. 477 - 477 (2008)
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Vierhapper,Eliel
, p. 2729,2733 (1975)
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Frankowski,A.,Streith,J.
, p. 427 - 432 (1977)
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The reaction of transdecahydroquinoline with molecular oxygen.
WITKOP
, p. 419 - 420 (1954)
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Convenient procedure for the α-methylation of simple pyridines
Broering, Martin,Kleeberg, Christian
, p. 3672 - 3682 (2008)
A convenient and straightforward laboratory procedure is presented for a highly selective mono-α-methylation of pyridines without reactive functional groups. The methylating agent is probably carbon monoxide/dihydrogen generated in situ from a high-boiling alcohol on a metal surface. The reaction is catalyzed by a Raney nickel catalyst at ambient pressure, which renders the protocol practicable in standard organic laboratories. The intrinsically high reaction temperature and long reaction times restrict the application to pyridine derivatives with less reactive substituents. The outcome of the reaction can be rationalized by the assumption of a simple heterogeneous mechanism. Copyright Taylor & Francis Group, LLC.
ALKALOIDS OF Nitraria komarovii SYNTHESIS OF NITRARINE AND ISONITRARINE
Tulyganov, T. S.,Ibragimov, A. A.
, p. 512 - 515 (1993)
The natural alkaloids nitrarine and isonitrarine with the new heterocyclic system 14,21-ethano-16-azayohimban have been synthesized.
Superacidic activation of quinoline and isoquinoline; their reactions with cyclohexane and benzene
Koltunov, Konstantin Yu.,Prakash, G.K. Surya,Rasul, Golam,Olah, George A.
, p. 7394 - 7397 (2007)
(Chemical Equation Presented) Quinoline (1) and isoquinoline (2), upon activation by strong acids, lead to intermediate N,C-diprotonated dications, which are involved in reactions with weak nucleophiles. Thus, 1 and 2 undergo selective ionic hydrogenation with cyclohexane in CF3SO 3H-SbF5, HBr-AlBr3-CH2Br 2, or HCl-AlCl3-CH2Cl2 acid systems to give their 5,6,7,8-tetrahydro derivatives. They also readily condense with benzene in the presence of HBr-AlBr3 or HCl-AlCl3 to provide 5,6,7,8-tetrahydro-5,7-diphenylquinoline (10) and 5,6,7,8-tetrahydro-6, 8-diphenylisoquinoline (12), respectively.
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Breitmaier,Bayer
, p. 3291 (1970)
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Proton Magnetic Resonance Studies of Compounds with Bridgehead Nitrogen. Part 39. Stereochemistry of Perhydropyrido-benzoxazines and the Conformational Equilibrium for Perhydropyridooxazine
Crabb, Trevor A.,Turner, Christopher H.
, p. 1778 - 1782 (1980)
The four diastereoisomeric perhydropyridobenzoxazines have been synthesised and their configurations assigned by 1H n.m.r. and i.r. spectroscopy and by kinetic studies of N-methylation.Comparisons of the 1H n.m.r. chemical shifts of proton α to nitrogen in these isomers suggested an equilibrium (CDCl3,25 deg C) for perhydropyridooxazine containing ca. 90percent of the trans-fused conformer.
Pyrolysis of Phenylalkylsulphonyl Azides and 2-Phenethyl Azidoformate. Selectivity of Sulphonylnitrenes and Contrast between Sulphonyl- and Carbonyl-nitrenes
Abramovitch, Rudolph A.,Hendi, Shivakumar B.,Kress, Albert O.
, p. 1087 - 1088 (1981)
Flash vacuum pyrolysis and solution thermolysis of PhnSO2N3 indicate that intramolecular addition to the phenyl group is preferred in solution, provided that up to an eight-membered sultam ring is formed, otherwise side-chain insertion results, while in the gas phase the latter process is favoured when n = 4, 5, but not 3; some 5,6,7,8-tetrahydroquinoline is obtained when n = 3 at 990 deg C, but 2-phenethyl azidoformate gave monomeric tetrahydro-1,3-oxazinoazepin-2-one and 4-phenyloxazolidinone, but no dihydrocyclopentapyridine, even at 900 deg C.
Pincerlike manganese complex and preparation method thereof, related ligand and preparation method thereof, catalyst composition and application
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Paragraph 0159-0165, (2021/07/31)
The invention discloses a pincerlike manganese complex, a preparation method thereof, a ligand for preparation, a preparation method of the ligand, a catalyst composition taking the complex as an active component and application of the catalyst composition. According to the pincerlike manganese complex, a cycloalkyl ring is introduced into a ligand framework, and by regulating and controlling the cyclic tension, flexibility and steric hindrance of the cycloalkyl ring, the reactivity and stability of the manganese metal center can be effectively adjusted, and the catalytic activity and substrate applicability of a manganese metal system are remarkably improved. The catalyst composition taking the pincerlike manganese complex as an active component has the advantages of high catalyst activity, wide substrate application range, mild reaction conditions and the like in the process of preparing quinoline or pyridine derivatives by catalyzing dehydrogenation coupling reaction of o-amino aromatic alcohol or gamma-amino alcohol, ketone or secondary alcohol; and the synthesis advantages of low cost and stable performance are embodied, the operation is simple, and the yield is high.
Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies
Lecroq, William,Schleinitz, Jules,Billoue, Mallaury,Perfetto, Anna,Gaumont, Annie-Claude,Lalevée, Jacques,Ciofini, Ilaria,Grimaud, Laurence,Lakhdar, Sami
, p. 1237 - 1242 (2021/06/01)
We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.
RhNPs supported onN-functionalized mesoporous silica: effect on catalyst stabilization and catalytic activity
Pulido-Díaz, Israel T.,Serrano-Maldonado, Alejandro,López-Suárez, Carlos César,Méndez-Ocampo, Pedro A.,Portales-Martínez, Benjamín,Gutiérrez-Alejandre, Aída,Salas-Martin, Karla P.,Guerrero-Ríos, Itzel
, p. 3289 - 3298 (2021/03/16)
Amine and nicotinamide groups grafted on ordered mesoporous silica (OMS) were investigated as stabilizers for RhNPs used as catalysts in the hydrogenation of several substrates, including carbonyl and aryl groups. Supported RhNPs on functionalized OMS were prepared by controlled decomposition of an organometallic precursor of rhodium under dihydrogen pressure. The resulting materials were characterized thoroughly by spectroscopic and physical techniques (FTIR, TGA, BET, SEM, TEM, EDX, XPS) to confirm the formation of spherical rhodium nanoparticles with a narrow size distribution supported on the silica surface. The use of nicotinamide functionalized OMS as a support afforded small RhNPs (2.3 ± 0.3 nm), and their size and shape were maintained after the catalyzed acetophenone hydrogenation. In contrast, amine-functionalized OMS formed RhNP aggregates after the catalytic reaction. The supported RhNPs could selectively reduce alkenyl, carbonyl, aryl and heteroaryl groups and were active in the reductive amination of phenol and morpholine, using a low concentration of the precious metal (0.07-0.18 mol%).
