2-nitro- and 2,4-dinitrobenzenesulfonamides as protecting groups for primary amines

Citation
K. Nihei et al., 2-nitro- and 2,4-dinitrobenzenesulfonamides as protecting groups for primary amines, SYNLETT, (7), 2001, pp. 1167-1169
Citations number
29
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
7
Year of publication
2001
Pages
1167 - 1169
Database
ISI
SICI code
0936-5214(200107):7<1167:2A2APG>2.0.ZU;2-#
Abstract
Procedures for the deprotection of the 2-nitro- and 2,4-dinitrobenzenesulfo namides to give the corresponding primary amines were developed. The 2-Nitr obenzenesulfonyl group was effectively removed by HSCH2CH2OH/DBU or PhSH/Cs 2CO3 in DMF under mild conditions to give the corresponding primary amines in high to excellent yield. For removal of the 2,4-dinitrobrnzenesulfonyl g roup, the use of thiol alone (HSCH2CH2OH or PhSH) was quite effective. Sele ctive deprotection of 2,4-dinitrobenzene-sulfonamide in the presence of 2-n itrobznzenesulfonamide has also been achieved.