Palladium-Assisted Multicomponent Synthesis of 2-Aryl-4-aminoquinolines and 2-Aryl-4-amino[1,8]naphthyridines

Abstract

A palladium-mediated multicomponent domino reaction leading to 2-aryl-4-amino-quinolines and 2-aryl-4-amino[1,8]naphthyridines is reported. The scope of the reaction was examined using carbon monoxide, two 2-ethynyl-arylamines, four aryl iodides, and 10 primary amines as substrates. The selection of the appropriate catalytic system was achieved testing several palladium/phosphine systems and overrides previously reported drawbacks associated with the use of primary amines in related reactions. Moreover several features concerning the role of both palladium [(0) and (II)] and phosphines are reported.

Synthesis of Heterocycles via Palladium-Catalyzed Carbonylations

“…249 The group of Rossi developed a palladium-catalyzed carbonylative synthesis of 2-aryl-4-aminoquinolines and 2-aryl-4-amino [1,8]naphthyridines. 250 This palladium-catalyzed domino reaction started from aryl iodides and amines leading to 2-aryl-4-amino-quinolines and 2-aryl-4-amino [1,8]naphthyridines (Scheme 80c). The scope of the reaction was examined using two 2-ethynylarylamines, four aryl iodides, and 10 primary amines as substrates.…”

Transition metals in organic synthesis: Highlights for the year 2005

“…Palladium catalyzed the formation of 2-aryl-4-aminoquinolines from 2-(1-alkyn-1-yl)benzenamines, carbon monoxide, and aryl iodides and an amine (Eq. (340)) [1441]. Palladium catalyzed the formation of pyridone derivatives from isoxazolidine-5-spirocyclopropanes.…”

Palladium‐Catalyzed Carbonylative Multicomponent Reactions

“…The groups of Torii and Rossi reported the four‐component synthesis of 2‐aryl‐4‐aminoquinolines and analogues, respectively, with the utilization of similar strategies involving a palladium‐catalyzed carbonylative Sonogashira reaction . Owing to the simultaneous presence of three nucleophilic moieties, one terminal acetylene and two amines, in one reaction system, the main challenge in this type of multicomponent process is the competition between a carbonylative Sonogashira reaction, a carbonylative amidation, and a Sonogashira reaction.…”