2439-04-5Relevant articles and documents
Preparation method of tetrahydroisoquinoline derivative
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Paragraph 0023; 0024, (2018/03/24)
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.
Investigations of reactions of selected azaarenes with radicals in water. 1. Hydroxyl and sulfate radicals
Beitz, Toralf,Bechmann, Wolfgang,Mitzner, Rolf
, p. 6760 - 6765 (2007/10/03)
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.
Structure and Stereochemistry of cis-Dihydro Diol and Phenol Metabolites of Bicyclic Azaarenes from Pseudomonas putida UV4
Boyd, Derek R.,Sharma, Narain D.,Dorrity, Michael R. J.,Hand, Mark V.,McMordie, R. Austin S.,et al.
, p. 1065 - 1072 (2007/10/02)
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.