Syntheses of large-membered macrocycles having multiple hydrogen bonding moieties

Hisashi Shimakoshi, Takayuki Kai, Isao Aritome, Yoshio Hisaeda

    Research output: Contribution to journalArticlepeer-review

    25 Citations (Scopus)


    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
    Issue number46
    Publication statusPublished - Nov 11 2002

    All Science Journal Classification (ASJC) codes

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry


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