Download PDF
Synlett 2001; 2001(7): 1167-1169
DOI: 10.1055/s-2001-15158
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2001 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >