Merging Electrochemical Synthesis and Post-Ugi Cyclization for the Synthesis of Diverse 4‑Imidazolidinones

Despite the appreciation for electro-organic synthesis, postmulticomponent reaction transformation chemistry rarely exploits this powerful technology. Herein, we explore post-Ugi cyclization reactions using N-centered radical-mediated intramolecular ipso cyclization to synthesize diverse spirocyclic...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-07, Vol.88 (13), p.9199-9212
Main Authors: Suwalka, Dinesh, Malviya, Bhanwar Kumar, Verma, Ved Prakash, Jassal, Amanpreet Kaur, Sharma, Siddharth
Format: Article
Language:English
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Summary:Despite the appreciation for electro-organic synthesis, postmulticomponent reaction transformation chemistry rarely exploits this powerful technology. Herein, we explore post-Ugi cyclization reactions using N-centered radical-mediated intramolecular ipso cyclization to synthesize diverse spirocyclic variants of 4-imidazolidinones through the use of electrochemically generated amidyl radicals from the bis-amides of the Ugi adducts. This protocol features an undivided cell setup under constant-current conditions with carbon–platinum electrodes. These metal- and reagent-free reactions are scalable and have broad substrate scope.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00772