Synthesis of 2,3-bis(perfluoroalkyl)quinoxalines and 2,3-bis(perfluoroalkyl)-1,4-benzoxazines from oxides of internal perfluoroolefins |
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Authors: | Lyudmila V Saloutina Aleksandr Ya Zapevalov Victor I Saloutin Mikhail I Kodess Valentina E Kirichenko Marina G Pervova Oleg N Chupakhin |
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Institution: | Institute of Organic Synthesis, Urals Branch of the Russian Academy of Sciences, 20/22 S. Kovalevskoy/Academicheskaya, GSP-147, 620219 Ekaterinburg, Russia |
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Abstract: | The reactions of oxides of internal trans-, cis-perfluoroolefins with o-phenylenediamine and 2-aminophenol in dioxane gave 2,3-bis(perfluoroalkyl)quinoxalines and 2,3-bis(perfluoroalkyl)-2H-1,4-benzoxazin-2-ols respectively in yields of 23-67%. When N,N-dimethylacetamide was used as a solvent an anionic isomerization of the oxides into ketones, which further yielded 2-(perfluoroalkyl)benzimidazoles in the case of o-phenylenediamine and 2-hydroxy-N-perfluoroalkanoylanilines in the case of 2-aminophenol, became the main path of these reactions. Unusual cyclization resulting in 2-pentafluoroethyl-2-pentafluoropropanoylbenzoxazolidine occurs on interaction between dodecafluoro-3,4-epoxyhexane and 2-aminophenol in N,N-dimethylacetamide. |
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Keywords: | Oxides of internal perfluoroolefins O-phenylenediamine 2-Aminophenol 2 3-Bis(perfluoroalkyl)quinoxalines 2 3-Bis(perfluoroalkyl)-1 4-benzoxazines 2-(Perfluoroalkyl)benzimidazoles 2-Hydroxy-N-perfluoroalkanoylanilines |
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