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Synthesis 2000; 2000(14): 2033-2038
DOI: 10.1055/s-2000-8724
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Facile and Versatile Synthesis of Polydentate Metal Chelators with Both Amide and Oxime Donor Groups

Michael J. Goldcamp* , Dell T. Rosa, Nicholas A. Landers, Sarah M. Mandel, Jeanette A. Krause Bauer, Michael J. Baldwin
  • *Department of Chemistry, University of Cincinnati, P. O. Box 21 01 72, Cincinnati, OH, 45221-0172, USA; Fax +(513)5 56 92 39; E-mail: michael.baldwin@uc.edu
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Publication History

Publication Date:
31 December 2000 (online)

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The first compounds with mixtures of deprotonateable amide and oxime donor groups that may act as tetradentate metal chelators were synthesized using the reagent N,N,N-triethyl-N-(propan-2-onyl oxime)ammonium chloride to add the oxime-containing arms to various amines with attached amides. This reagent avoids the complications due to competition between deprotonation of the oxime moiety and acid/base chemistry of the alkylation reaction. These compounds are based on either the simple "tripodal amine" framework, or on chiral, natural amino acid derivatives. The steric properties may be easily tuned by variation of the "R-groups" on the arms containing the functional groups.

amide - oxime - chelate - alkylation - amino acid

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