NOVEL PREPARATION METHOD OF QUINOLINE N-OXIDE DERIVATIVE WITH AMIDE GROUP
Provided are a preparation method of a quinoline N-oxide derivative with an amide group capable of easily introducing the amide group into the quinoline N-oxide derivative by simplified processes and mild reaction conditions, and a quinoline N-oxide derivative with an amide group prepared by using the same.
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Paragraph 138; 139
(2015/11/09)
Regioselective introduction of heteroatoms at the C-8 position of quinoline N-oxides: Remote C-H activation using N-oxide as a stepping stone
Reported herein is the metal-catalyzed regioselective C-H functionalization of quinoline N-oxides at the 8-position: direct iodination and amidation were developed using rhodium and iridium catalytic systems, respectively. Mechanistic study of the amidation revealed that the unique regioselectivity is achieved through the smooth formation of N-oxide-chelated iridacycle and that an acid additive plays a key role in the rate-determining protodemetalation step. While this approach of remote C-H activation using N-oxide as a directing group could readily be applied to a wide range of heterocyclic substrates under mild conditions with high functional group tolerance, an efficient synthesis of zinquin ester (a fluorescent zinc indicator) was demonstrated.
A mild palladium-catalyzed Suzuki coupling reaction of quinoline carboxylates with boronic acids
A palladium-catalyzed cross-coupling between aryl carboxylates and boronic acids has been achieved for the first time by taking advantage of the enhanced reactivity of quinoline 4-carboxylates. Also for the first time a Suzuki coupling reaction via a self-activation of boronic acids without addition of base is described. The reactions proceed under mild conditions (25-65°C) to give excellent yields, and a wide range of functionalities is tolerated. Copyright
Li, Wenjie,Gao, Joe J.,Zhang, Yongda,Tang, Wenjun,Lee, Heewon,Fandrick, Keith R.,Lu, Bruce,Senanayake, Chris H.
supporting information; experimental part
p. 1671 - 1675
(2011/09/20)
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