Syntheses of large-membered macrocycles having multiple hydrogen bonding moieties

Hisashi Shimakoshi, Takayuki Kai, Isao Aritome, Yoshio Hisaeda

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

New macrocyclic compounds have been synthesized by Schiff-base condensation reaction with methylenebis(4,4′-methyl-6,6′-salicylaldehyde) and 1,2-bis(2-aminoethoxy)ethane based on a high dilution method. [2+2], [3+3], and [4+4]-Cyclocondenced products were effectively isolated and characterized by 1H NMR and HR mass (FAB) spectroscopies as well as X-ray analyses. Reduction of the macrocycles with NaBH4 afforded the corresponding multi-amino, multi-phenolic macrocyclic compounds. The reduced molecules have low energy barriers for conformation change, which are estimated by variable-temperature (VT) 1H NMR study.

Original languageEnglish
Pages (from-to)8261-8264
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number46
DOIs
Publication statusPublished - Nov 11 2002

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Macrocyclic Compounds
Hydrogen Bonding
Hydrogen bonds
Nuclear magnetic resonance
Ethane
Condensation reactions
Schiff Bases
Energy barriers
X ray spectroscopy
Dilution
Conformations
Mass Spectrometry
X-Rays
Molecules
Temperature
Proton Magnetic Resonance Spectroscopy

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Syntheses of large-membered macrocycles having multiple hydrogen bonding moieties. / Shimakoshi, Hisashi; Kai, Takayuki; Aritome, Isao; Hisaeda, Yoshio.

In: Tetrahedron Letters, Vol. 43, No. 46, 11.11.2002, p. 8261-8264.

Research output: Contribution to journalArticle

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