Synthesis and properties of imidazolo-fused benzotriazinyl radicals

Andrey A. Berezin, Christos P. Constantinides, Styliana I. Mirallai, Maria Manoli, Levy L. Cao, Jeremy M. Rawson, Panayiotis A. Koutentis

Research output: Contribution to journalArticlepeer-review


1,3-Diphenylbenzo[e][1,2,4]triazin-7(1H)-one, the oxidation product of 1,3-diphenyl-1,4-dihydro-1,2,4-benzotriazin-4-yl (Blatter's radical), reacts with N′-arylbenzamidines in PhMe at ca. 100 °C in the presence of N,N-diisopropylethylamine (Hünig's base) (1 equiv.) to give N′-aryl-N-(1,7-dihydro-7-oxo-1,3-diphenylbenzo[e][1,2,4]triazin-6-yl) benzimidamides in 49-95% yield. In neat AcOH heated at ca. 120 °C, N′-aryl-N-(1,7-dihydro-7-oxo-1,3-diphenylbenzo[e][1,2,4]triazin-6-yl) benzimidamides cyclodehydrate to give the novel 8-substituted 1,3,7-triphenyl-4,8-dihydro-1H-imidazo[4,5-g][1,2,4]benzotriazin-4-yls in 13-81% yield. During the optimization of this cyclodehydration an additional oxazole fused benzotriazinyl radical 1,3,7-triphenyl-1,4-dihydro[1,3]oxazolo[4,5-g][1,2, 4]benzotriazin-4-yl was isolated as a side product and characterized. The CV and EPR data of the imidazolo- and oxazolo-fused radicals are presented as well as single crystal X-ray structures of 1,3,7-triphenyl-1,4-dihydro-[1,3]oxazolo[4,5- g][1,2,4]benzotriazin-4-yl and 1,3,7,8-tetraphenyl-4,8-dihydro-1H-imidazo[4,5-g] [1,2,4]benzotriazin-4-yl.

Original languageEnglish
Pages (from-to)6780-6795
Number of pages16
JournalOrganic and Biomolecular Chemistry
Issue number39
Publication statusPublished - 21 Oct 2013


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