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

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

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

Keywords

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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

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.",

keywords = "Aza-Wittig reactions, Cycloaddition, Planar-chirality, Pyridine-formation reactions, Pyridinophanes",

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

year = "2006",

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T1 - Synthesis of bridged nicotinates having [n](2,5)pyridinophane skeletons (n=8-14)

AU - Kanomata, Nobuhiro

AU - Yamada, Shinsuke

AU - Ohhama, Takayuki

AU - Fusano, Akira

AU - Ochiai, Yoshiharu

AU - Oikawa, Jun

AU - Yamaguchi, Masahiro

AU - Sudo, Fumio

PY - 2006/4/24

Y1 - 2006/4/24

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.

KW - Aza-Wittig reactions

KW - Cycloaddition

KW - Planar-chirality

KW - Pyridine-formation reactions

KW - Pyridinophanes

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