- Preparation method of tetrahydroisoquinoline derivative
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The invention discloses a preparation method of a tetrahydroisoquinoline derivative which is N-Fmoc-1,2,3,4-tetrahydroisoquinoline-5-alcohol. The preparation method comprises the following steps: taking isoquinoline as a starting raw material, loading sulfonic acid groups, hydrolyzing, hydrogenating and carrying out Fmoc protection to obtain a target product. The compound is used as an important medical intermediate.
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Paragraph 0023; 0024
(2018/03/24)
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- Copper-catalyzed hydrolysis of bromoisoquinolines: Preparation of hydroxyisoquinolines
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A complex phenomenon was observed in the process of preparing hydroxyisoquinoline through copper-catalyzed hydrolysis of bromoisoquinoline. The copper (II) complexes of hydroxyisoquinoline (L2Cu.5H2O) were characterized by high resolution mass spectra, thermogravimetric analysis, IR, 1H nuclear magnetic resonance (NMR), and 2D-NMR. The Cu (II) complexes were mononuclear and coordinated with oxygen and nitrogen atom of two hydroxyisoquinoline and five water molecules in which a strong hydrogen bond was present. Two optimized methods had been studied to prevent the formation of copper (II) complexes. The isoquinoline with 4, 5, 6, 7, and 8 hydroxyl substitutions were successfully prepared by copper-catalyzed hydrolysis of corresponding bromoisoquinoline and then workup by sodium sulfide or adjusted pH by dry ice or carbon dioxide gas.
- Xingjun, Jiang,Jianbo, He,Hongli, Chen,Weiqing, Yang,Yuanyuan, Zhang,Menglin, Ma
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- Investigations of reactions of selected azaarenes with radicals in water. 1. Hydroxyl and sulfate radicals
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The oxidative degradation of binuclear azaarenes is studied in a number of environmentally relevant radical reactions. The comparison between oxidation mechanisms of hydroxyl and sulfate radicals, as well as between dark and photoreactions, is done. Most of the products formed are identified. With the change from dark to photoreactions of quinoline and isoquinoline, a shift of the oxidation center from the benzene to the pyridine rings is observed. The reaction behavior of the benzodiazines can be derived from the reaction patterns of quinoline and isoquinoline. The rate constants of second order are determined for the reactions of the azaarenes with carbonate radicals. The rate constants and the differences in the products formed conformably prove the importance of the inclusion of excited states in the reaction mechanism. The application of the frontier orbital concept allows an easy interpretation. Electron transfer reactions resulting in radical oxygen species are shown to be product determining in direct photolysis, too.
- Beitz, Toralf,Bechmann, Wolfgang,Mitzner, Rolf
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p. 6760 - 6765
(2007/10/03)
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- SYNTHESIS OF POTENTIAL &β-BLOCKERS DERIVED FROM 5-HYDROXYISOQUINOLINE
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The synthesis of N-substituted amides 5-hydroxyisoquinaldate is described.Keywords: 5-hydroxyisoquinoline derivatives, synthesis, elemental and spectral analysis.
- Walczynski, Krzysztof,Glinka, Ryszard
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p. 479 - 482
(2007/10/02)
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- Structure and Stereochemistry of cis-Dihydro Diol and Phenol Metabolites of Bicyclic Azaarenes from Pseudomonas putida UV4
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Biotransformation of quinoline, isoquinoline, quinoxaline and quinazoline using growing cultures of Pseudomonas putida UV4 yielded cis-dihydro diols from the oxidation of the carbocyclic aromatic ring.Aromatic hydroxylation was observed in both carbocyclic and heterocyclic rings.Ring cleavage of the quinoline skeleton to yield anthranilic acid, and cis-diol formation (with alkene bond reduction) to yield cis-5,6,7,8-tetrahydroquinazoline-5,6-diol from quinazoline were observed.The cis-dihydro diol metabolites of quinoline (5,6- and 7,8-) and quinoxaline (5,6-) were found to be optically pure, while metabolism of isoquinoline gave on e homochiral (5,6-) and one racemic 7,8-) cis-dihydro diol product.The absolute configuration of the cis-dihydro diol metabolites have been determined using 1H NMR analyses, stereochemical correlations and X-ray crystallography methods.
- Boyd, Derek R.,Sharma, Narain D.,Dorrity, Michael R. J.,Hand, Mark V.,McMordie, R. Austin S.,et al.
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p. 1065 - 1072
(2007/10/02)
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- Synthesis of Arene Oxide and trans-Dihydro Diol Metabolites of Isoquinoline
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5,6-Epoxy-5,6-dihydroisoquinoline 9 and 7,8-epoxy-7,8-dihydroisoquinoline 21 were each obtained by multi-step synthetic sequences from 5,6,7,8-tetrahydroisoquinoline 1.The mammalian metabolite, trans-5,6-dihydroisoquinoline-5,6-diol 10 was chemically synthesised by base-catalysed hydration of the isoquinoline arene oxide 9.
- Boyd, Derek R.,Davies, R. Jeremy H.,Hamilton, Lynne,McCullough, John J.
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- Metabolism of Bicyclic Aza-arenes by Pseudomonas putida to Yield Vicinal cis-Dihydrodiols and Phenols
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Metabolism of the aza-arenes quinoline, isoquinoline, quinazoline, and quinoxaline by a mutant strain of the bacterium Pseudomonas putida resulted in attack at the carbocyclic ring (to yield stable cis-dihydrodiols and phenols) and at the heterocyclic ring (to yield phenols and ring cleavage products).
- Boyd, Derek R.,McMordie, R. Austin S.,Porter, H. Patricia,Dalton, Howard,Jenkins, Richard O.,Howarth, Oliver W.
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p. 1722 - 1724
(2007/10/02)
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