4.7 Article

Electrochemical Post-Ugi Cyclization for the Synthesis of Highly Functionalized Spirolactams

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JOURNAL OF ORGANIC CHEMISTRY
卷 88, 期 19, 页码 13977-13994

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c01532

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The combination of the Ugi reaction and electro-organic synthesis has been used to develop a new strategy for the synthesis of novel heterocycles with diverse functional groups. This approach offers high selectivity and is applicable for large-scale synthesis.
The combination of the Ugi reaction and electro-organic synthesis can aid in the creation of novel heterocycles that have not been previously explored. In this study, a new strategy utilizing bis-amides from the Ugi reaction has been developed, which can produce C-S, C-Se, and C-C=O functionalized five-membered spirolactams mediated by electricity under catalyst- and metal-free conditions. Notably, this approach can be applied using a microelectro-flow reactor (mu-EFR) for gram-scale synthesis. The described strategy can synthesize complex azaspiro-fused tricyclic scaffolds with high diastereo- and regioselectivity, highlighting its versatility and potential.

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