Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, P. R. China.
Chem Commun (Camb). 2020 Mar 25;56(24):3488-3491. doi: 10.1039/d0cc00923g. Epub 2020 Mar 12.
A novel protocol for the construction of functionalized (Z)-3-(1(-arylamino)-2-oxoarylidene)indolin-2-ones (AOIDOs) from isatins 1 with nitro-substituted enamines 2via an unprecedented cascade reaction catalyzed by sulfamic acid is developed. The AOIDOs are prepared by simply refluxing a mixture of isatins with a wide variety of nitro-substituted enamines. Interestingly, the AOIDOs 3 were formed through the novel cascade reaction involving a unique cleavage of two C-N bonds of the nitro-substituted enamines. Overall, the novel reaction is accomplished by the formation of three new bonds and the cleavage of two C-N bonds in a single step. This protocol can be used in the synthesis of a wide variety of AOIDOs and is suitable for combinatorial and parallel syntheses of natural-like AOIDO products.
发展了一种新颖的由色胺酮 1 与硝基取代烯胺 2 通过磺酸催化的前所未有的级联反应构建功能化 (Z)-3-(1-芳基氨基-2-氧代亚烯基)吲哚啉-2-酮 (AOIDO) 的新方法。通过简单回流色胺酮与各种硝基取代烯胺的混合物即可制备 AOIDO。有趣的是，AOIDO 3 通过涉及硝基取代烯胺的两个独特 C-N 键断裂的新型级联反应形成。总体而言，新反应通过单个步骤形成三个新键和两个 C-N 键的断裂来完成。该方案可用于广泛的 AOIDO 的合成，并且适合于天然样 AOIDO 产物的组合和并行合成。
