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Issue 14, 2011
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1,3-Diphenylbenzo[e][1,2,4]triazin-7(1H)-one: Selected Chemistry at the C-6, C-7 and C-8 Positions

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Abstract

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.

Graphical abstract: 1,3-Diphenylbenzo[e][1,2,4]triazin-7(1H)-one: Selected Chemistry at the C-6, C-7 and C-8 Positions

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Publication details

The article was received on 15 Mar 2011, accepted on 13 Apr 2011 and first published on 13 Apr 2011


Article type: Paper
DOI: 10.1039/C1OB05410D
Org. Biomol. Chem., 2011,9, 5228-5237

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    1,3-Diphenylbenzo[e][1,2,4]triazin-7(1H)-one: Selected Chemistry at the C-6, C-7 and C-8 Positions

    P. A. Koutentis, H. Krassos and D. Lo Re, Org. Biomol. Chem., 2011, 9, 5228
    DOI: 10.1039/C1OB05410D

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