Synthesis of 4- and 6-substituted nitroindoles |
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Authors: | Nikolai Moskalev |
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Affiliation: | Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44, PO Box 58, 01-224 Warszawa 42, Poland |
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Abstract: | Enolizable ketones react with m-nitroaniline in the presence of strong base such as t-BuOK to give 4- and 6-substituted nitroindoles. The reaction proceeds via oxidative nucleophilic substitution of hydrogen in m-nitroaniline with enolate anions in positions ortho to the amino group giving anionic σH adducts that are additionally stabilized by intramolecular interaction between the amino and the carbonyl group. Spontaneous oxidation of the σH adducts followed by the Bayer type condensation of the produced ortho-aminonitrobenzyl ketones gives 4- and 6-substituted nitroindoles. The scope of this reaction and its basic mechanistic features are discussed. |
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Keywords: | Enolates Indoles Nitroarenes Nucleophilic addition |
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