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Three‐Component Radical Iodonitration of 1,6‐Enynes to Access Iodo‐ and Nitro‐ Di‐Functionalized 4‐Enyl‐2‐Pyrrolidones

Herein, we report a three‐component radical cascade cyclization reaction for the synthesis of iodo‐ and nitro‐di‐functionalized 4‐enyl‐2‐pyrrolidones with 1,6‐enynes under metal‐free and catalyst‐free conditions. In this reaction, the (Z) configuration… Click to show full abstract

Herein, we report a three‐component radical cascade cyclization reaction for the synthesis of iodo‐ and nitro‐di‐functionalized 4‐enyl‐2‐pyrrolidones with 1,6‐enynes under metal‐free and catalyst‐free conditions. In this reaction, the (Z) configuration products with high stereoselectivity are obtained. Meanwhile, this strategy is useful for the synthesis of di‐functionalized lactams, and heterocyclic products have huge potential biological activities. The control experiments indicate that the cascade cyclization is realized by radical reactions, as well as the detailed reaction mechanism and regioselectivities have been explained by DFT studies.

Keywords: functionalized enyl; nitro functionalized; enyl pyrrolidones; three component; iodo nitro; component radical

Journal Title: Journal of Heterocyclic Chemistry
Year Published: 2025

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