Study on the reactions of fluoroalkanesulfonyl azides with indole derivatives |
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Authors: | Ping He |
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Affiliation: | a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, PR China b College of Chemical Environment, South China Normal University, Guangzhou 510631, China |
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Abstract: | The reactions of fluoroalkanesulfonyl azides 1 with different indole derivatives have been studied in detail. Treatment of 1 with equimolar amount of 1,3-dimethylindole 3 in 1,4-dioxane at room temperature afforded 2-(1,3-dimethyl-1,3-dihydro-indolinylidene) fluoroalkanesulfonylimines 5 in moderate to good yields. However, under the same reaction conditions, in the case of 1 with 1,2-dimethylindole 4, the corresponding 2-fluoroalkanesulfonyl (1,2-dimethyl-1H-indol-3-yl)-amide 6 was obtained in moderate yields. In addition, the reactions of 1 and indole 7 gave different products under different conditions. Possible mechanisms of these reactions were proposed. |
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Keywords: | Fluoroalkanesulfonyl azides Indole derivatives 1,3-Dipolar cycloaddition Triazolines Diazo transfer |
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