Download PDF
Synthesis 1995; 1995(8): 1019-1026
DOI: 10.1055/s-1995-4043
paper
© 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.

Synthesis of Bicyclic Polyaza Polycarboxylic Macrocycles Containing a 12-Membered Unit

Vincent Jacques, Mohammed Mesbahi, Verica Boskovic, Jean F. Desreux*
  • *Coordination and Radiochemistry, University of Liège, Sart Tilman (B6), B-4000 Liège, Belgium, Fax +32(41)663364; E-mail U211501@VM1.ULG.AC.BE
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

High dilution reactions between a diamine and a diacid activated with 1,3-thiazolidine-2-thione afforded bicyclic polyamines after reduction of the amido moieties with borane. The cyclisation yields ranged between 34 and 84% and presumably depend on the rigidity of the reagents. Selection of the most appropriate procedures for the deprotection of tosylated amino groups and for the addition of carboxylic groups appear to depend on the structure and the cavity size of the macrocycles. For instance, encapsulation of a Na+ ion as seen by 23Na NMR prevents the substitution of the secondary amino groups of the polyaza ligands by acetate functions.

Polyaza polycarboxylic bis-macrocycles are synthesized from a diprotected tetraaza cyclic unit.