Synthesis and Complexation Properties of Pyrimidine-Derived Crown Ether Ligands [1]

J. Ty Redd, Jerald S. Bradshaw, P. Huszthy, Reed M. Izatt, N. Kent Dalley

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Five new proton-ionizable macrocyclic ligands containing a pyrimidone-subcyclic unit, 6-10, were prepared from the previously prepared pyrimidinocrown ethers 1-5 (see Figure 1 and Scheme 1). One of the new proton-ionizable crown ethers is chiral. The proton-ionizable pyrimidonocrown ethers were prepared in high yields by treating the appropriate methoxy-substituted pyrimidinocrown with 5 M sodium hydroxide in a 50% alcohol-water mixture. Complexation properties of four of the pyrimidine-derived macrocycles were studied by various nmr techniques. Pyrimidono-18-crown-6 (9) forms a strong complex with benzylammonium perchlorate and also forms a complex with benzylamine. (S,S)-Dimethyl-substituted pyrimidino- and pyrimidono-18-crown-6 ligands 4 and 9 form stronger complexes with the (R)-form of α-(1-naphthyl)ethyl-ammonium perchlorate than with the (S)-form. (S,S)-Dimethyl-substituted pyrimidono-18-crown-6 (9) also forms a stronger complex with (R)-α-(1-naphthyl)ethylamine than with the (S)-form. The crystal structure for compound 7 is reported.

Original languageEnglish
Pages (from-to)1-8
Number of pages8
JournalJournal of Heterocyclic Chemistry
Volume35
Issue number1
Publication statusPublished - 1998

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Crown Ethers
Complexation
Protons
Ethers
Ligands
Pyrimidinones
Sodium Hydroxide
Crystal structure
Alcohols
Water
pyrimidine
18-crown-6

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and Complexation Properties of Pyrimidine-Derived Crown Ether Ligands [1]. / Redd, J. Ty; Bradshaw, Jerald S.; Huszthy, P.; Izatt, Reed M.; Dalley, N. Kent.

In: Journal of Heterocyclic Chemistry, Vol. 35, No. 1, 1998, p. 1-8.

Research output: Contribution to journalArticle

Redd, J. Ty ; Bradshaw, Jerald S. ; Huszthy, P. ; Izatt, Reed M. ; Dalley, N. Kent. / Synthesis and Complexation Properties of Pyrimidine-Derived Crown Ether Ligands [1]. In: Journal of Heterocyclic Chemistry. 1998 ; Vol. 35, No. 1. pp. 1-8.
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AB - Five new proton-ionizable macrocyclic ligands containing a pyrimidone-subcyclic unit, 6-10, were prepared from the previously prepared pyrimidinocrown ethers 1-5 (see Figure 1 and Scheme 1). One of the new proton-ionizable crown ethers is chiral. The proton-ionizable pyrimidonocrown ethers were prepared in high yields by treating the appropriate methoxy-substituted pyrimidinocrown with 5 M sodium hydroxide in a 50% alcohol-water mixture. Complexation properties of four of the pyrimidine-derived macrocycles were studied by various nmr techniques. Pyrimidono-18-crown-6 (9) forms a strong complex with benzylammonium perchlorate and also forms a complex with benzylamine. (S,S)-Dimethyl-substituted pyrimidino- and pyrimidono-18-crown-6 ligands 4 and 9 form stronger complexes with the (R)-form of α-(1-naphthyl)ethyl-ammonium perchlorate than with the (S)-form. (S,S)-Dimethyl-substituted pyrimidono-18-crown-6 (9) also forms a stronger complex with (R)-α-(1-naphthyl)ethylamine than with the (S)-form. The crystal structure for compound 7 is reported.

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