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

doi:10.1055/s-2003-40359

LETTER

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;

Abstract

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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.

Key words

arenes - amino acids - Diels-Alder reactions - polycycles

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References

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

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