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Updated: Oct 27, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Copper/silver co-mediated three-component bicyclization for accessing indeno[1,2-c]azepine-3,6-diones
Shi-Chao Wang1, Peng-Yu Liu1, Yi-Xin Chen1
1School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, 221116, P. R. China. wjhao@jsnu.edu.cn laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn.
Abstract:
A new copper/silver-co-mediated three-component bicyclization of benzene-linked 1,6-enynes with ICF2CO2Et with TMSN3 was reported, and used to produce a wide range of hitherto unreported difluorinated tetrahydroindeno[1,2-c]azepine-3,6-diones with moderate to good yields. The mechanistic pathway consists of radical-induced 1,6-addition-cyclization, oxidative addition, reductive elimination, nitrene insertion and N-O cleavage, resulting in continuous multiple bond-forming events including C-C and C-N bonds to build up a 6/5/7 tricyclic framework.
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