1H and13C NMR conformational study of N-substituted hexahydrocyclopent[e] [1,3]-oxazin-4-ones and hexahydro-2H-1,3-benzoxazin-4-ones

Roustem A. Shaikhutdinov, Karel D. Klika, Ferenc Fülöp, Kalevi Pihlaja

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A 1H and 13C NMR conformational study of four cis-fused N-substituted hexahydrocyclopent[e][1,3]oxazin4-ones and four cis-fused hexahydro-2H-1,3-benzoxazin-4-ones at various temperatures revealed several dynamic conformational processes to be in effect. These included a clear conformational equilibrium between the O-in (major conformer) and O-out ring forms in the hexahydro-2H-1,3-benzoxazin-4-ones, an equilibrium consisting of two intramolecularly hydrogen bonded forms (between the hydroxyl proton and the carbonyl oxygen attached to C4 or the ethereal oxygen) and a non-hydrogen bonded form in two compounds, and a restricted rotation about the amide C-N bond in the CH2OCONHC6H4X-p substituents (X = H, Cl) in three other compounds.

Original languageEnglish
Pages (from-to)141-146
Number of pages6
JournalMagnetic Resonance in Chemistry
Volume39
Issue number3
DOIs
Publication statusPublished - Jan 1 2001

Keywords

  • Conformational analysis
  • Heterocycles
  • Hydrogen bonding
  • NMR
  • Restricted rotation
  • c nmr
  • h nmr

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)

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