Modular Three-Component Synthesis of 4-Aminoquinolines via an Imidoylative Sonogashira/Cyclization Cascade
We developed a one-pot, two-stage synthetic route to substituted 4-aminoquinolines involving an imidoylative Sonogashira coupling followed by acid-mediated cyclization. This three-component reaction affords pharmaceutically valuable 4-aminoquinolines in a one-pot procedure from readily available starting materials. The reaction tolerates various substituents on the arene as well as the use of secondary and even primary isocyanides. Additionally, the wide tolerance for functionalized isocyanides allows for the one-pot synthesis of various substituted chloroquine analogues as well as other medicinally relevant products.
Collet, Jurri?n W.,Ackermans, Kelly,Lambregts, Jeffrey,Maes, Bert U.W.,Orru, Romano V.A.,Ruijter, Eelco
An Unusual Base-Mediated Cyclization of Ketimines Derived from 2-(Trifluoromethyl)aniline That Involves the Trifluoromethyl Group: An Expedient Route to 2-Arylquinolines
6-(Substituted methylene)-N-(arylalkylidene)-2,4-cyclohexadien-1-imines, such as 13, 17, and 21 (Scheme II) are suggested intermediates in a novel synthetic route to 2-arylquinolines based on the reaction of trifluoromethyl-substituted ketimines, such as
Strekowski, Lucjan,Wydra, Roman L.,Cegla, Marek T.,Czarny, Agnieszka,Harden, Donald B.,et al.
p. 4777 - 4779
(2007/10/02)
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