American Chemical Society
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One-Step Synthesis of Hydropyrrolo[3,2‑b]indoles via Cascade Reactions of Oxindole-Derived Nitrones with Allenoates

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journal contribution
posted on 2022-11-10, 18:35 authored by Meng-Lan Luo, Qiumeng Hou, Shuai-Jiang Liu, Qian Zhao, Rui Qin, Cheng Peng, Bo Han, Gu Zhan
Hydropyrrolo[2,3-b]indole is a privileged indoline motif, while its analogue, hydropyrrolo[3,2-b]indole, has been much less explored. Herein, we developed a cascade reaction of oxindole-derived nitrones with allenoates, providing straightforward access to the tetracyclic hydropyrrolo[3,2-b]indole scaffolds. Formation of multiple C–C/C–X bonds and cleavage could be achieved within one synthetic step using a simple catalyst (Gimeracil) under mild conditions. The reaction pathway may involve the generation of spiro-hydroazepinone as the key intermediate.