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2,4-Dinitrobenzenesulfonamides: A simple and practical method for the preparation of a variety of secondary amines and diamines

✍ Scribed by Tohru Fukuyama; Mui Cheung; Chung-Kuang Jow; Yuko Hidai; Toshiyuki Kan


Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
191 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis


2,4-Dinitrobenzenesulfonamides, readily prepared from primary amines and 2,4-dinitrobenzenesulfonyl chloride, can be alkylated by the Mitsunobu reaction or by the conventional methods to give N,N-disubstituted sulfonamides in excellent yields. Since 2,4-dinitrobenzenesulfonamides can be removed without deproteeting 2-nitrobenzenesulfonamides, a wide variety of diamines could be prepared by the combined use of these protecting/activating groups.


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Difficulties encountered in the synthesis of resin-bound secondary amines attached via an acid-labile linker encouraged us to employ an alternative approach. A one-pot, scalable procedure for the synthesis of Fmoc-protected, amine/linker constructs is reported. These compounds can be efficiently cou