59953-98-9Relevant articles and documents
ELECTROPHILIC REACTIONS OF 3-HYDROXYQUINOLINE-1-OXIDE
Gol'tsova, L. V.,Lezina, V. P.,Kuz'min, V. I.,Smirnov, L. D.
, p. 1522 - 1524 (1984)
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Synthesis of 8-Aminoquinolines by Using Carbamate Reagents: Facile Installation and Deprotection of Practical Amidating Groups
Gwon, Donghyeon,Hwang, Heejun,Kim, Hye Kyung,Marder, Seth R.,Chang, Sukbok
supporting information, p. 17200 - 17204 (2016/01/25)
Described herein is the development of practical routes to 8-aminoquinolines by using readily installable and easily deprotectable amidating reagents. Two scalable procedures were optimized under RhIII-catalyzed conditions: i) the use of pre-generated chlorocarbamates and ii) a two-step one-pot process that directly employs carbamates. Both approaches are highly convenient for the gram-scale synthesis of 8-aminoquinolines under mild conditions. Facile deprotection of the synthetically versatile amidating groups was achieved under the Pd-catalyzed transfer hydrogenation conditions with simultaneous deoxygenation of quinoline N-oxides, thus yielding 8-aminoquinolines in excellent overall efficiency.
KINETICS OF N-OXIDATION OF COMPOUNDS OF THE QUINOLINE SERIES AND ISOMERIC BENZOQUINOLINES BY PERBENZOIC ACID IN CHLOROFORM AND AQUEOUS DIOXANE
Lokhov, R. E.
, p. 72 - 76 (2007/10/02)
The kinetics of the N-oxidation with perbenzoic acid of 15 derivatives of quinoline and benzoquinoline in chloroform and 19 compounds in 50percent aqueous dioxane at 20, 25, 30, and 35 deg C were subjected to a comparative study.The rate constants, parameters of Arrhenius equation, and the activation energies for the N-oxidation of the indicated monoazines were determined.A scale of the reactivities of derivatives of the quinoline series and benzoquinolines was calculated within the framework of general perturbation theory.