Download PDF
Synthesis 1995; 1995(4): 453-457
DOI: 10.1055/s-1995-3923
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 Ester Derivatives of 1,4,7-Triazacyclononane-1,4,7-tris(methylenephosphonic Acid) and 1,4,7-Triazacyclononane-1,4,7-tris(methyleneethylphosphinic Acid)

István Lázár1 , A. Dean Sherry2
  • 1Department of Inorganic and Analytical Chemistry, Lajos Kossuth University, Debrecen-10, P.O. Box 21, H-4010, Hungary
  • 2Department of Chemistry, The University of Texas at Dallas, P.O. Box 830688, Richardson, Texas 75083-0688, USA
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Two methods have been developed for the synthesis of new 1,4,7-triazacyclononanetris(methylenephosphonic acid) (3-6, 8-11) and -tris(methyleneethylphosphinic acid) (7, 12) ester derivatives. The first procedure includes the synthesis of 2 in anhydrous THF which can then be used as a useful synthetic intermediate for several new derivatives of 1,4,7-triazacyclononane (1). In the second procedure, compound 1 and dialkyl phosphite or ethyl ethylphosphinate are reacted with paraformaldehyde in refluxing benzene yielding the corresponding esters in good to excellent yield. New macrocyclic complexing agents 8-12 have been prepared by either basic (8-11) or acidic (12) hydrolysis of the corresponding ester derivatives, or directly from the starting macrocycle 12. Side reactions decreasing the yield and purity of the products are also discussed.

macrocycles - 1,4,7-triazacyclononane - Mannich reaction - phosphorus - NMR probes