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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
Cyclization of substitued 2-(2-fluorophenylazo)azines to azino[1,2-c]benzo[d][1,2,4]triazinium derivatives
Aleksandra Jankowiak1, Emilia Obijalska, Piotr Kaszynski
1Organic Materials Research Group, Department of Chemistry, Vanderbilt University, Nashville, TN 37235, USA.
Abstract:
Light-induced cyclization of several substituted 2-(2-fluorophenylazo)azines in the presence of Ca(2+) ions to the corresponding triazinium derivatives is investigated experimentally and computationally. The azo derivatives of 4-methylpyridine 4 undergo facile cyclization to the corresponding triazinium 1, and the rate of cyclization increases with increasing number of fluorine atoms at the benzene ring. No triazinium ions were obtained from azo derivatives of 4-cyanopyridine, pyrazine and pyrimidine, presumably due to their instability under the reaction conditions. The experimental results and mechanism are discussed with the aid of DFT computational results.
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