Synlett 2003(9): 1361-1363
DOI: 10.1055/s-2003-40359
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Rigid Polycyclic Secondary Diamines: Bis-(2,3:6,7-Imino­dimethylene)anthracene and Bis-(2,3:6,7-Iminodimethylene)-9,10-dicarboxy­ethenoanthracene

Sumita Bhattacharyya, Jörgen Toftered, Ulf J. Nilsson*
Organic and Bioorganic Chemistry, Lund University, POB 124, SE-221 00 Lund, Sweden
Fax: +46(46)2228209; e-Mail: ulf.nilsson@bioorganic.lth.se;
Weitere Informationen

Publikationsverlauf

Received 17 March 2003
Publikationsdatum:
30. Juni 2003 (online)

Abstract

The synthesis of two rigid polycyclic secondary diamines, bis-(2,3:6,7-iminodimethylene)anthracene and bis-(2,3:6,7-iminodimethylene)-9,10-dicarboxyethenoanthracene, by means of Diels-Alder reaction between 1,2,4,5-tetra(dibromo­methyl)benzene and maleimides followed by imide reduction, is described. Furthermore, these two cyclic secondary diamines undergo acylation with N-protected amino acids, thus providing functionalized, amphiphilic, and chiral building blocks for incorporation into supramolecular systems.