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)

I. Lazar, A. D. Sherry

Research output: Contribution to journalArticle

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Abstract

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.

Original languageEnglish (US)
Pages (from-to)453-457
Number of pages5
JournalSynthesis
Issue number4
Publication statusPublished - 1995

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Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

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