Amphoteric 2-(sulfonylamino)benzaldehydes,secondary amines and isocyanides in the multicomponent synthesis of elusive N-alkyl-2,3-diaminoindoles |
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Authors: | Mariateresa Giustiniano Sveva Pelliccia Luca Sangaletti Fiorella Meneghetti Jussara Amato Ettore Novellino Gian Cesare Tron |
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Institution: | 1. Dipartimento di Farmacia, Università di Napoli “Federico II”, via D. Montesano 49, 80131 Napoli, Italy;2. Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale, Largo Donegani 2, 28100 Novara, Italy;3. Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, Via L. Mangiagalli 25, 20133 Milano, Italy |
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Abstract: | A novel interrupted Ugi reaction between ortho-sulfonylaminated aryl aldehydes, secondary amines, and isocyanides affords in good to high yields N-alkyl-2,3-diaminoindoles, providing access to a so far unexplored area of the indole chemical space. With only one single chemical operation, this novel reaction affords a broad gamma of substituted 2,3-diaminoindoles with five points of diversity. The success of this novel multicomponent transformation lies in presence of the amphoteric sulfonylamino group, which sequentially acts as a Brønsted acids and as a nucleophile the lack of need for additional catalysts and the high atom economy, with the loss of only one molecule of water, renders this approach a very effective one. |
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Keywords: | Multicomponent reactions 2-(Sulfonylamino)benzaldehyde Isocyanides Secondary amines 3-Diaminoindoles |
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