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Synthesis of 8‐Aminoquinolines by Using Carbamate Reagents: Facile Installation and Deprotection of Practical Amidating Groups
Author(s) -
Gwon Donghyeon,
Hwang Heejun,
Kim Hye Kyung,
Marder Seth R.,
Chang Sukbok
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503511
Subject(s) - deoxygenation , reagent , combinatorial chemistry , quinoline , chemistry , aminoquinolines , catalysis , carbamate , organic chemistry
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 Rh III ‐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.