2-nitro- and 2,4-dinitrobenzenesulfonamides as protecting groups for primary amines
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Undergraduate course
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Publisher
Georg Thieme Verlag Kg
Type
Article
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Acesso restrito
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Abstract
Procedures for the deprotection of the 2-nitro- and 2,4-dinitrobenzenesulfonamides to give the corresponding primary amines were developed. The 2-Nitrobenzenesulfonyl group was effectively removed by HSCH2CH2OH/DBU or PhSH/Cs2CO3 in DMF under mild conditions to give the corresponding primary amines in high to excellent yield. For removal of the 2,4-dinitrobrnzenesulfonyl group, the use of thiol alone (HSCH2CH2OH or PhSH) was quite effective. Selective deprotection of 2,4-dinitrobenzene-sulfonamide in the presence of 2-nitrobznzenesulfonamide has also been achieved.
Description
Keywords
2-nitrobenzenesulfonamide, 2,4-dinitrobenzenesulfonamide, protecting groups, deprotection, primary amines
Language
English
Citation
Synlett. Stuttgart: Georg Thieme Verlag Kg, n. 7, p. 1167-1169, 2001.
