Rapid construction of tricyclic tetrahydrocyclopenta[4,5]pyrrolo[2,3- b ]pyridine via isocyanide-based multicomponent reaction

作者：Xiuyu Chen, Ying Han, Jing Sun, Chao‐Guo Yan · 发表于：Beilstein Journal of Organic Chemistry · 年份：2024 · DOI：10.3762/bjoc.20.126 · 被引用次数：9 · 研究领域：Multicomponent Synthesis of Heterocycles、Synthesis and Characterization of Pyrroles、Synthesis and Reactivity of Heterocycles

An efficient protocol for the synthesis of polyfunctionalized tetrahydrocyclopenta[4,5]pyrrolo[2,3- b ]pyridine-3,4b,5,6,7(1 H )-pentacarboxylates was developed by a three-component reaction. In the absence of any catalyst, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 5,6-unsubstituted 1,4-dihydropyridines in refluxing acetonitrile afforded polyfunctionalized tetrahydrocyclopenta[4,5]pyrrolo[2,3- b ]pyridine-3,4b,5,6,7(1 H )-pentacarboxylates in high yields and with high diastereoselectivity. The reaction was finished by in situ generation of activated 5-(alkylimino)cyclopenta-1,3-dienes from addition of alkyl isocyanide to two molecules of but-2-ynedioates and sequential formal [3 + 2] cycloaddition reaction with 5,6-unsubstituted 1,4-dihydropyridine.