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

doi:10.1016/j.tet.2006.02.002

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)

Abstract

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, (S_p,S)-14 and (R_p,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 language	English
Pages (from-to)	4128-4138
Number of pages	11
Journal	Tetrahedron
Volume	62
Issue number	17
DOIs	https://doi.org/10.1016/j.tet.2006.02.002
Publication status	Published - 2006 Apr 24

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Keywords

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. https://doi.org/10.1016/j.tet.2006.02.002

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abstract = "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.",

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AU - Fusano, Akira

AU - Ochiai, Yoshiharu

AU - Oikawa, Jun

AU - Yamaguchi, Masahiro

AU - Sudo, Fumio

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N2 - 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.

AB - 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.

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Access to Document

10.1016/j.tet.2006.02.002