Synthesis of new proton-ionizable crown ether compounds containing substituted 1H-pyridin-4-one subcyclic units

P. Huszthy, Julia Kertesz, Jerald S. Bradshaw, Reed M. Izatt, J. Ty Redd

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Five novel pyridono-18-crown-6 (10-14) and two new benzyloxy-substituted pyridino-18-crown-6 (15 and 16) ligands have been prepared. By the catalytic hydrogenative removal of the benzyl group from the benzyloxy moiety at position 4 of the pyridine ring of 15 and 16, pyridono-18-crown-6 ethers 5 and 12 were obtained. These ligands were transformed to their 3,5-dibromo (10 and 13) and 3,5-dinitro derivatives (11 and 14) by treatment with bromine in methylene chloride and nitric acid in acetic anhydride, respectively. The latter proton-ionizable crown ethers have pKa values of about 7.5 for 10 and 13 and 4.5 for 11 and 14. Thus, they are good candidates for complexation and proton-coupled transport of selected cations.

Original languageEnglish
Pages (from-to)1259-1264
Number of pages6
JournalJournal of Heterocyclic Chemistry
Volume38
Issue number6
Publication statusPublished - 2001

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Crown Ethers
Protons
Ligands
Nitric Acid
Bromine
Ethers
Methylene Chloride
Complexation
Cations
Derivatives
18-crown-6

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of new proton-ionizable crown ether compounds containing substituted 1H-pyridin-4-one subcyclic units. / Huszthy, P.; Kertesz, Julia; Bradshaw, Jerald S.; Izatt, Reed M.; Ty Redd, J.

In: Journal of Heterocyclic Chemistry, Vol. 38, No. 6, 2001, p. 1259-1264.

Research output: Contribution to journalArticle

Huszthy, P. ; Kertesz, Julia ; Bradshaw, Jerald S. ; Izatt, Reed M. ; Ty Redd, J. / Synthesis of new proton-ionizable crown ether compounds containing substituted 1H-pyridin-4-one subcyclic units. In: Journal of Heterocyclic Chemistry. 2001 ; Vol. 38, No. 6. pp. 1259-1264.
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AB - Five novel pyridono-18-crown-6 (10-14) and two new benzyloxy-substituted pyridino-18-crown-6 (15 and 16) ligands have been prepared. By the catalytic hydrogenative removal of the benzyl group from the benzyloxy moiety at position 4 of the pyridine ring of 15 and 16, pyridono-18-crown-6 ethers 5 and 12 were obtained. These ligands were transformed to their 3,5-dibromo (10 and 13) and 3,5-dinitro derivatives (11 and 14) by treatment with bromine in methylene chloride and nitric acid in acetic anhydride, respectively. The latter proton-ionizable crown ethers have pKa values of about 7.5 for 10 and 13 and 4.5 for 11 and 14. Thus, they are good candidates for complexation and proton-coupled transport of selected cations.

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