Ring opening of 2-(bromomethyl)-1-sulfonylaziridines towards 1,3-heteroatom substituted 2-aminopropane derivatives |
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Authors: | Matthias D'hooghe |
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Institution: | Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium |
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Abstract: | 1,3-Heteroatom substituted 2-aminopropane derivatives have been prepared from 2-(bromomethyl)-1-sulfonylaziridines for the first time using sodium azide or different potassium phenoxides in water in the presence of silica gel. The applicability of 1-arenesulfonyl-2-(bromomethyl)aziridines for the synthesis of functionalized sulfonamides has also been demonstrated towards different 1,3-dialkoxy-2-(tosylamino)propanes and 1,3-dialkylthio-2-(tosylamino)propanes upon treatment with the appropriate sodium alkoxide or sodium alkylthiolate in the corresponding alcohol or in methanol, respectively. |
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Keywords: | 2-(Bromomethyl)aziridines 2-Aminopropanes Water Ring opening Nucleophiles |
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