Abstract

A new ring opening reaction was found while attempting to isolate the imines from ortho-heteroatom substituted anilines and camphor-like bicyclic ketones. The benzoazoles containing a cyclopentanemethyl group at position 2 of the heterocycle were isolated instead of the expected imines. The detailed study of the transformation, including EPR experiments, revealed the most probable radical mechanism. The proposed reaction pathways were confirmed by quantum chemical calculations. The dichotomy of 1–2 and 2–3 bonds cleavage is discussed together with the evaluation of the stereochemical outcome of the reactions. The benzoazoles obtained via the new reaction are of particular interest for the medicinal chemistry.

Original languageEnglish
Pages (from-to)452-463
Number of pages12
JournalEuropean Journal of Organic Chemistry
Volume2021
Issue number3
Early online date27 Dec 2020
DOIs
Publication statusPublished - 22 Jan 2021

Keywords

  • (−)-Fenchone
  • Benzimidazoles
  • Camphor
  • Monoterpenoids
  • Single-stage synthesis
  • AUXILIARY BASIS-SETS
  • NONNUCLEOSIDE INHIBITORS
  • BENZIMIDAZOLE DERIVATIVES
  • DOCKING
  • MEDIATED SYNTHESIS
  • BENZOXAZOLE
  • MOLECULES
  • BIOLOGICAL EVALUATION
  • HIV-1 REVERSE-TRANSCRIPTASE
  • ANTIFUNGAL
  • (&#8722
  • )-Fenchone

OECD FOS+WOS

  • 1.04 CHEMICAL SCIENCES

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