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

Research output: Contribution to journalArticlepeer-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, (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
JournalTetrahedron
Volume62
Issue number17
DOIs
Publication statusPublished - 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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