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

Autor: Nagar R; Department of Chemistry, Mohanlal Sukhadia University, Udaipur 313001, India., Suwalka D; Department of Chemistry, Mohanlal Sukhadia University, Udaipur 313001, India., Malviya BK; Department of Chemistry, Mohanlal Sukhadia University, Udaipur 313001, India., Verma VP; Department of Chemistry, Banasthali University, Niwai-Jodhpuriya Road, Vanasthali 304022, India., Jassal AK; Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry, Guru Nanak Dev University, Amritsar 143005, India., Sharma S; Department of Chemistry, Mohanlal Sukhadia University, Udaipur 313001, India.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2023 Oct 06; Vol. 88 (19), pp. 13977-13994. Date of Electronic Publication: 2023 Sep 11.
DOI: 10.1021/acs.joc.3c01532
Abstrakt: 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.
Databáze: MEDLINE