Synthesis of bridged nicotinates having [n](2,5)pyridinophane skeletons (n=8-14)

Nobuhiro Kanomata, Shinsuke Yamada, Takayuki Ohhama, Akira Fusano, Yoshiharu Ochiai, Jun Oikawa, Masahiro Yamaguchi, Fumio Sudo

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    12 Citations (Scopus)


    Synthesis of various bridged nicotinates 6 having [n](2,5)pyridinophane skeletons (n=8-14) was accomplished by the unique pyridine-formation reaction of methyl propiolate with a series of formyl-substituted (vinylimino)phosphoranes 5, which were prepared from the corresponding cycloalkanones 1 via Vilsmeier-Haack formylation giving chloro-substituted cycloalkenals 2, their thermal and photochemical transformation to formyl azirines 4, and the following ring-opening reactions with triphenylphosphine. The HPLC analysis of [11](2,5)pyridinophane derivatives, (Sp,S)-14 and (Rp,S)-14, showed that these diastereomers rapidly epimerize themselves at room temperature and that their planar-chirality was thermodynamically less stable as compared to the corresponding [11](2,5)cyclophane systems.

    Original languageEnglish
    Pages (from-to)4128-4138
    Number of pages11
    Issue number17
    Publication statusPublished - 2006 Apr 24



    • Aza-Wittig reactions
    • Cycloaddition
    • Planar-chirality
    • Pyridine-formation reactions
    • Pyridinophanes

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Kanomata, N., Yamada, S., Ohhama, T., Fusano, A., Ochiai, Y., Oikawa, J., Yamaguchi, M., & Sudo, F. (2006). Synthesis of bridged nicotinates having [n](2,5)pyridinophane skeletons (n=8-14). Tetrahedron, 62(17), 4128-4138.