American Chemical Society
ol7b03803_si_002.pdf (17.38 MB)

Cascade Reaction of Isatins with 1,1-Enediamines: Synthesis of Multisubstituted Quinoline-4-carboxamides

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journal contribution
posted on 2018-01-11, 14:47 authored by Bao-Qu Wang, Cong-Hai Zhang, Xiao-Xue Tian, Jun Lin, Sheng-Jiao Yan
A one-step methodology for the synthesis of multisubstituted quinoline-4-carboxamides was developed by simply refluxing a mixture of isatins 1 and various kinds of 1,1-enediamines 24 in a reaction catalyzed by NH2SO3H. As a result, a series of quinolone-4-carboxamides were produced through a novel cascade reaction mechanism. This reaction involved the formation of the quinoline ring accompanied by the formation of an amide bond in one step. Accordingly, this protocol is suitable for combinatorial and parallel syntheses of quinolone-4-carboxamide drugs or natural products.