The stereoselective synthesis of highly functionalized tertiary 3-aminoindoles/anilines or dihydropyrroles from C-(3-indolyl)-N-aryl and C,N-diaryl nitrones |
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Authors: | VS Velezheva VN Azev AS Peregudov Yu L Sebyakin |
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Affiliation: | a A. N. Nesmeyanov Institute of Organoelement compounds, Russian Academy of Sciences, Vavilov Str. 28, 119991 Moscow, Russia b M. V. Lomonosov Moscow State Academy of Fine Chemical Technology, 86 Vernadskogo Str., 119571 Moscow, Russia |
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Abstract: | We report on the novel properties of nitrones including their transformations via reactions with sodium malonates to give functionalized stereodefined derivatives of tertiary 3-aminoindoles or anilines, as well as fully-substituted dihydropyrroles. The outcome of the reactions is dependent mainly upon the nature of the starting C-nitrone substituent and solvent used. The formation of a new carbon-nitrogen bond in the obtained amines occurs via a nucleophilic 1,2-aryl/3-indolyl shift from C to the adjacent nitrogen. |
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