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Updated: May 7, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Dipolar Cycloaddition of Cyclopropene with N,N-Cyclic Azomethine Imine: A Straightforward Protocol for
Meng-Ge Ding1, Wenyu Gao1, Chuang Zhao1
1College of Chemistry and Life Sciences, Changchun University of Technology, Changchun, Jilin 130012, P. R. China.
Abstract:
The [3 + 2] dipolar cycloaddition reaction between cyclopropene and N,N-cyclic azomethine imine is reported, offering an efficient protocol for the construction of the diazabicyclo[3.1.0]hexane skeleton. This method features good yields, robust functional group tolerance (62 examples), and diastereoselectivity. In vitro antiproliferative activity screening of the product library against five strains of tumor cell lines (HL-60, A549, HepG2, MDA-MB-231, and SW480) showed that the scaffold exhibits promising proliferation inhibitory effects. Among them, the HL-60 cell line is the most sensitive with IC50 values being as low as 8.05 ± 0.40 μM. An SAR analysis of these compounds is presented.
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