1316792-97-8Relevant academic research and scientific papers
Redox Active Quinoidal 1,2,4-Benzotriazines
Zissimou, Georgia A.,Kourtellaris, Andreas,Manoli, Maria,Koutentis, Panayiotis A.
, p. 9391 - 9402 (2018/07/05)
Modifying the para-quinonimine 1,3-diphenyl-1,2,4-benzotriazin-7(1H)-one (2a) (E1/2-1/0 -1.20 V), by replacing the N1-phenyl by pentafluorophenyl, the C3-phenyl by trifluoromethyl, or the C7 carbonyl by ylidenemalononitrile, led to improved electron affinities as determined by cyclic voltammetry and computational studies. Combining structural changes further improved electron accepting abilities: the most electron deficient analogues (E1/2-1/0 ～ -0.65 V) involved combining the ylidenemalononitrile groups at C7 with the trifluoromethyl groups at C3. 1,2,5-Thiadiazolo fusion at C5-C6 did not affect the redox behavior but did enhance the UV-vis absorption profile. During the synthesis of the thiadiazolo analogues, 1,4-thiazino-fused analogues 6 were obtained in low yield, which thermally ring contract to the triazafluoranthenones 7. Compounds are fully characterized, and X-ray data are provided for selected analogues.
Effective exchange coupling in alternating-chains of a π-extended 1,2,4-benzotriazin-4-yl
Constantinides, Christos P.,Berezin, Andrey A.,Manoli, Maria,Leitus, Gregory M.,Bendikov, Michael,Rawson, Jeremy M.,Koutentis, Panayiotis A.
, p. 949 - 954 (2014/03/21)
Air stable 1,3,7-triphenyl-1,4-dihydrothiazolo[5′,4′:4,5] benzo[1,2-e][1,2,4]triazin-4-yl packs in 1D π stacks made of radical pairs with alternate short and long interplanar distances. The magnetic susceptibility exhibits a broad maximum at 73 ± 5 K and
Synthesis and properties of imidazolo-fused benzotriazinyl radicals
Berezin, Andrey A.,Constantinides, Christos P.,Mirallai, Styliana I.,Manoli, Maria,Cao, Levy L.,Rawson, Jeremy M.,Koutentis, Panayiotis A.
, p. 6780 - 6795 (2013/10/01)
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 (Hu?nig'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.
Some cyclization reactions of 1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one: Preparation and computational analysis of non symmetrical zwitterionic biscyanines
Ioannou, Theodosia A.,Koutentis, Panayiotis A.,Krassos, Harry,Loizou, Georgia,Re, Daniele Lo
experimental part, p. 1339 - 1348 (2012/03/27)
Regioselective nucleophilic addition of bisnucleophiles 1,2-benzenediamine, 2-amino-benzenethiol, and N-phenyl-1,2-benzenediamine to 1,3-diphenylbenzo[e] [1,2,4]triazin-7(1H)-one (1) at C6 followed by intramolecular cyclocondensation at the C7 carbonyl af
From blatter radical to 7-substituted 1,3-diphenyl-1,4- dihydrothiazolo[5′,4′:4,5]benzo[1,2-e][1,2,4]triazin-4-yls: Toward multifunctional materials
Berezin, Andrey A.,Constantinides, Christos P.,Drouza, Chryssoula,Manoli, Maria,Koutentis, Panayiotis A.
supporting information, p. 5586 - 5589 (2013/01/15)
A Blatter radical is oxidized to benzotriazin-7(H)-one which after amination and subsequent acyl- and aroylation gives N-(benzotriazin-6-yl) carboxamides that undergo ring closure with P2S5 to afford the corresponding thiazolo[5′,4′:
1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one: Selected chemistry at the C-6, C-7 and C-8 positions
Koutentis, Panayiotis A.,Krassos, Harry,Lo Re, Daniele
supporting information; experimental part, p. 5228 - 5237 (2011/09/14)
1,3-Diphenylbenzo[e][1,2,4]triazin-7(1H)-one (6) reacts with tetracyanoethylene (TCNE) or tetracyanoethylene oxide (TCNEO) to give the deep green 2-[1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-ylidene]propanedinitrile (11) in 17 and 15% yields, respectively. Nucleophiles such as amines, alkoxides, thiols and Grignard reagents all reacted with the 1,3-diphenylbenzotriazinone 6 regioselectively at C-6, while halogenating agents reacted exclusively at C-8. Furthermore, 8-iodo-1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one (32) undergoes palladium-catalysed Suzuki-Miyaura and Stille coupling reactions to give 8-aryl- or heteroaryl-substituted benzotriazinones. By combining both the C-6 and C-8 chemistries 1,3,6,8-tetraphenylbenzo[e][1,2,4]triazin-7(1H)-one (42) and 1,3-diphenyl-6,8-di(thien-2-yl)-benzo[e][1,2,4]triazin-7(1H)-one (43) can be prepared. All new compounds are fully characterized. The Royal Society of Chemistry 2011.
