N-Aryl-2-nitrosoanilines as intermediates in the synthesis of substituted phenazines from nitroarenes |
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Authors: | Andrzej KwastKarolina Stachowska Adam TrawczyńskiZbigniew Wróbel |
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Institution: | a Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44, 01-224 Warszawa 42, Poland b Faculty of Chemistry, Warsaw University of Technology, Warszawa, Poland |
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Abstract: | N-Aryl-2-nitrosoanilines, available from the reaction of nitroarenes with anilide anions, undergo cyclization to furnish substituted phenazines. The reaction is promoted by potassium carbonate in methanol, N,O-bis(trimethylsilyl)acetamide (BSA) in aprotic solvents, and by acetic acid. The method is illustrated by the synthesis of 1-methoxyphenazine, a precursor of pyocyanine, starting from the appropriate nitroarene-aniline pairs. |
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Keywords: | Heterocycles Nitroso group Cyclization |
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