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Updated: Sep 26, 2025

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Published on: January 3, 2018
Revisiting the Synthesis of Functionally Substituted 1,4-Dihydrobenzo[e][1,2,4]triazines
Margarita A Epishina1, Alexander S Kulikov1, Leonid L Fershtat1
1Laboratory of Nitrogen Compounds, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp., 47, 119991 Moscow, Russia.
Abstract:
A series of novel 1,4-dihydrobenzo[1,2,4][e]triazines bearing an acetyl or ester moiety as a functional group at the C(3) atom of the 1,2,4-triazine ring were synthesized. The synthetic protocol is based on an oxidative cyclization of functionally substituted amidrazones in the presence of DBU and Pd/C. It was found that the developed approach is suitable for the preparation of 1,4-dihydrobenzo[e][1,2,4]triazines, but the corresponding Blatter radicals were isolated only in few cases. In addition, a previously unknown dihydrobenzo[e][1,2,4]triazolo[3,4-c][1,2,4]triazine tricyclic open-shell derivative was prepared. Studies of thermal behavior of the synthesized 1,4-dihydrobenzo[1,2,4][e]triazines revealed their high thermal stability (up to 240-250 °C), which enables their application potential as components of functional organic materials.
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