Issue 39, 2013

Synthesis and properties of imidazolo-fused benzotriazinyl radicals

Abstract

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.

Graphical abstract: Synthesis and properties of imidazolo-fused benzotriazinyl radicals

Supplementary files

Additions and corrections

Article information

Article type
Paper
Submitted
06 Jun 2013
Accepted
12 Aug 2013
First published
12 Aug 2013

Org. Biomol. Chem., 2013,11, 6780-6795

Synthesis and properties of imidazolo-fused benzotriazinyl radicals

A. A. Berezin, C. P. Constantinides, S. I. Mirallai, M. Manoli, L. L. Cao, J. M. Rawson and P. A. Koutentis, Org. Biomol. Chem., 2013, 11, 6780 DOI: 10.1039/C3OB41169A

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