Iminium Ion and N-Hydroxyimide as the Surrogate Components in DEAD-Promoted Oxidative Ugi Variant.

J Org Chem

Key Laboratory of Drug Metabolism and Pharmacokinetics , China Pharmaceutical University, 24 Tongjia Xiang , Nanjing 210009 , Jiangsu , China.

Published: November 2018

A practical metal-free oxidative Ugi-type three-component assembly has been achieved efficiently, employing a tertiary-amine-derived iminium ion as an imine surrogate, N-hydroxyimide as an acid surrogate, and DEAD as an oxidant. This dual-surrogate Ugi variant proceeded with a broad substrate scope and desired functional group tolerance, leading to a wide range of N-alkyl- N-acyl aminophthalimide and N-alkyl- N-acylaminosuccinimide derivatives in good isolated yields.

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Source
http://dx.doi.org/10.1021/acs.joc.8b01868DOI Listing

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