Issue 14, 2020

One-pot construction of functionalized aziridines and maleimides via a novel pseudo-Knoevenagel cascade reaction

Abstract

An Ugi, novel pseudo-Knoevenagel, ring expansion cascade reaction was discovered and utilized for the synthesis of aziridinyl succinimides in one-pot. Subsequently, densely functionalized aziridines and maleimides have been designed and synthesized through similar cascade reactions. The target compounds were prepared by means of a mild reaction and a simple operation procedure, which could be applicable to a broad scope of starting materials. This series of novel cascade reactions generates opportunities for the tailored synthesis of a wide range of biologically active scaffolds through tuneable Ugi inputs. Discovery of compound 8i with comparable potency to sorafenib in liver cancer cell lines could provide a new avenue for liver cancer drug discovery.

Graphical abstract: One-pot construction of functionalized aziridines and maleimides via a novel pseudo-Knoevenagel cascade reaction

Associated articles

Supplementary files

Article information

Article type
Communication
Submitted
22 Oct 2019
Accepted
24 Dec 2019
First published
11 Jan 2020

Chem. Commun., 2020,56, 2194-2197

One-pot construction of functionalized aziridines and maleimides via a novel pseudo-Knoevenagel cascade reaction

J. Lei, G. Song, L. He, Y. Luo, D. Tang, H. Lin, B. Frett, H. Li, Z. Chen and Z. Xu, Chem. Commun., 2020, 56, 2194 DOI: 10.1039/C9CC08220D

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