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.
Compounds with Bridgehead Nitrogen. Part 49. The Synthesis and Stereochemistry of Perhydropyridobenzoxazepines and of r-3a,t-11a,c-14a,t-14b,t-22a,t-22b-Perhydrodiquinodioxadiazacyclotetradecine
Crabb, Trevor A.,Jupp, Philip A.
, p. 913 - 918 (1985)
Ring closure of the diastereoisomeric 2-decahydroquinolin-8-ylethanols with formaldehyde gave r-4a,c-7a,t-11a-, r-4a,t-7a,t-11a, and r-4a,c-7a,c-11a-perhydropyridobenzoxazepines, but instead of the fourth isomer a dimer, r-3a,t-11a,c-14a,t-14b,t-22a,t-22b-perhydrodiquinodioxadiazacyclotetradecine, was obtained.Comparison of 13C n.m.r. shifts of the conformationally locked isomers with those of perhydropyridooxazepine showed different average perhydro-1,3-oxazepine ring conformations in the various structures so that an estimate of the position of conformational equilibrium (CDCl3 solution) of the bicyclic compound from this data could not be made.The 13C n.m.r. spectrum of perhydropyridooxazepine in CDCl3-CFCl3, however, showed a ratio of ca. 5:1 trans-fused:O-inside-cis-fused conformers at -80 oC.
Asymmetric synthesis of myrioxazines A and B, novel alkaloids of Myrioneuron nutans
Pham, Van Cuong,Jossang, Akino,Chiaroni, Angèle,Sévenet, Thierry,Bodo, Bernard
, p. 7565 - 7568 (2002)
Two new epimeric tricyclic alkaloids, myrioxazines A and B were isolated from the leaves of Myrioneuron nutans and their structures elucidated by spectral analysis (mass spectrometry and 2D NMR). Absolute configurations were determined by total asymmetric synthesis.
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.
Convenient synthesis of cobalt nanoparticles for the hydrogenation of quinolines in water
Beller, Matthias,Dorcet, Vincent,Fischmeister, Cedric,Hervochon, Julien,Junge, Kathrin
, p. 4820 - 4826 (2020)
Easily accessible cobalt nanoparticles are prepared by hydrolysis of NaBH4 in the presence of inexpensive Co(ii) salts. The resulting material is an efficient catalyst for the hydrogenation of quinoline derivatives in water. The activity and chemoselectivity of this catalyst are comparable to other cobalt-based heterogeneous catalysts.
