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

Riya Nagar, Dinesh Suwalka, Bhanwar Kumar Malviya, Ved Prakash Verma, Amanpreet Kaur Jassal, Siddharth Sharma

2023The Journal of Organic Chemistry19 citationsDOI

Abstract

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 (μ-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.

Topics & Concepts

ElectrochemistryChemistryCombinatorial chemistryElectrodePhysical chemistryMulticomponent Synthesis of HeterocyclesSynthetic Organic Chemistry MethodsOxidative Organic Chemistry Reactions
Electrochemical Post-Ugi Cyclization for the Synthesis of Highly Functionalized Spirolactams | Litcius