1,3-Diphenylbenzo[e][1,2,4]triazin-7(1H)-one: Selected Chemistry at the C-6, C-7 and C-8 Positions
| Autor: | Koutentis, Panayiotis Andreas, Krassos, H., Lo Re, D. |
|---|---|
| Přispěvatelé: | Koutentis, Panayiotis Andreas [0000-0002-4652-7567] |
| Rok vydání: | 2011 |
| Předmět: |
Grignard reagent
Tetracyanoethylene Oxide chemistry.chemical_element Alkoxides Biochemistry Medicinal chemistry Chemical reaction Suzuki-Miyaura chemistry.chemical_compound Nucleophile Computational chemistry Chemical reactions Stille coupling reaction Physical and Theoretical Chemistry Organic Chemistry Chemical bonds Propanedinitrile Stille reaction chemistry Chemical bond Reagent Human echovirus 1 Palladium Nucleophiles |
| Zdroj: | Organic and Biomolecular Chemistry Org.Biomol.Chem. |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/c1ob05410d |
| Popis: | 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. 9 14 5228 5237 Cited By :11 |
| Databáze: | OpenAIRE |
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