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

    研究成果: Article

    12 引用 (Scopus)

    抄録

    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.

    元の言語English
    ページ(範囲)4128-4138
    ページ数11
    ジャーナルTetrahedron
    62
    発行部数17
    DOI
    出版物ステータスPublished - 2006 4 24

    Fingerprint

    Azirines
    Phosphoranes
    Chirality
    Skeleton
    Hot Temperature
    High Pressure Liquid Chromatography
    Derivatives
    Temperature
    cyclophane 2
    pyridine
    triphenylphosphine

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    これを引用

    Kanomata, N., Yamada, S., Ohhama, T., Fusano, A., Ochiai, Y., Oikawa, J., ... Sudo, F. (2006). Synthesis of bridged nicotinates having [n](2,5)pyridinophane skeletons (n=8-14). Tetrahedron, 62(17), 4128-4138. https://doi.org/10.1016/j.tet.2006.02.002

    Synthesis of bridged nicotinates having [n](2,5)pyridinophane skeletons (n=8-14). / Kanomata, Nobuhiro; Yamada, Shinsuke; Ohhama, Takayuki; Fusano, Akira; Ochiai, Yoshiharu; Oikawa, Jun; Yamaguchi, Masahiro; Sudo, Fumio.

    :: Tetrahedron, 巻 62, 番号 17, 24.04.2006, p. 4128-4138.

    研究成果: Article

    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, 巻. 62, 番号 17, pp. 4128-4138. https://doi.org/10.1016/j.tet.2006.02.002
    Kanomata, Nobuhiro ; Yamada, Shinsuke ; Ohhama, Takayuki ; Fusano, Akira ; Ochiai, Yoshiharu ; Oikawa, Jun ; Yamaguchi, Masahiro ; Sudo, Fumio. / Synthesis of bridged nicotinates having [n](2,5)pyridinophane skeletons (n=8-14). :: Tetrahedron. 2006 ; 巻 62, 番号 17. pp. 4128-4138.
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    AU - Fusano, Akira

    AU - Ochiai, Yoshiharu

    AU - Oikawa, Jun

    AU - Yamaguchi, Masahiro

    AU - Sudo, Fumio

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