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Synlett 2001; 2001(7): 1167-1169
DOI: 10.1055/s-2001-15158
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2-Nitro- and 2,4-Dinitrobenzenesulfonamides as Protecting Groups for Primary Amines

Ken-ichi Nihei* , Massuo J. Kato, Tetsuo Yamane, Mario S. Palma, Katsuhiro Konno
  • *Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes, 748, São Paulo, SP 05508-900, Brazil; Fax + 55-19-534-85 23; E-mail: kk-gon@rc.unesp.br
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Publication Date:
31 December 2001 (online)

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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-dinitrobenzenesulfonyl group, the use of thiol alone (HSCH2CH2OH or PhSH) was quite effective. Selective deprotection of 2,4-dinitrobenzenesulfonamide in the presence of 2-nitrobenzenesulfonamide has also been achieved.

2-nitrobenzenesulfonamide - 2,4-dinitrobenzenesulfonamide - protecting groups - deprotection - primary amines