2003
DOI: 10.1055/s-2003-37354
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Synthesis of (Indol-3-yl)methanesulfonamide and its 5-Methoxy Derivative

Abstract: Two methods for the synthesis of (indol-3-yl)methanesulfonamide were elaborated based on the 'switching off' the reactivity of the indole nucleus in the intermediates by using indoline or indoxyl compounds. (2,3-Dihydroindol-3-yl)methanesulfonic acid was the key compound used in the indole-indoline approach and (1-acetyl-3-hydroxy-2,3-dihydroindol-3-yl)-N-(tert-butyl)methanesulfonamide was the key intermediate when 1-acetylindoxyl was used as the starting compound. (1-Acetyl-3-hydroxy-2,3-dihydroindol-3-yl)-N-… Show more

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“…The generation of nucleophilic reagents by ionization of C-H and N-H groups is a common method in organic synthesis. Metalation of methanesulfonamide derivatives allows for the synthesis of aliphatic sulfonamides with complex structures that are difficult to obtain with other methods [ 26 , 27 , 28 ]. Therefore, we use the metalation of methanesulfonamide as a useful approach to obtain the key intermediate 6 for the synthesis of the target compound 7 .…”
Section: Resultsmentioning
confidence: 99%
“…The generation of nucleophilic reagents by ionization of C-H and N-H groups is a common method in organic synthesis. Metalation of methanesulfonamide derivatives allows for the synthesis of aliphatic sulfonamides with complex structures that are difficult to obtain with other methods [ 26 , 27 , 28 ]. Therefore, we use the metalation of methanesulfonamide as a useful approach to obtain the key intermediate 6 for the synthesis of the target compound 7 .…”
Section: Resultsmentioning
confidence: 99%