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Updated: May 12, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
The Studies on the Synthesizing Dibenzodiazocinediimine via Constructing an Eight-Membered Ring
Bing Wang1, Mengyao Mi1, Shu-Jia Li1
1Department of Chemistry, College of Chemistry and Materials Science, Jinan University, Guangzhou 510632, China.
Abstract:
A one-step and facile strategy to synthesize dibenzo[b,f][1,5]diazocine-6,12(5H,11H)-diimine and its analogs via the construction of an eight-membered ring has been established using o-aminobenzonitrile or o-phenylenediamine/phthalonitrile derivatives as raw materials. Twelve compounds, including 9 new compounds, have been synthesized in yields ranging from 62-95%. Five new compounds of 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-diimine derivatives have also been synthesized in yields of 35-52%. Furthermore, the reaction between arylnitriles and various amines was also efficiently established under similar reaction conditions. Finally, a reasonable mechanism involving sodium as a proper base to initiate the cyclization process was proposed.
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