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

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...

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Veröffentlicht in:Journal of organic chemistry 2018-11, Vol.83 (21), p.13121-13131
Hauptverfasser: Wang, Jiankun, Sun, Yilin, Jiang, Mu-Han, Hu, Tian-Yu, Zhao, Yong-Jie, Li, Xin, Wang, Guangji, Hao, Kun, Zhen, Le
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01868