Preparation and steric structure elucidation of partially saturated isoindolo[2,1-α][3,1]benzoxazinones and -[1,2-b][2,4]benzoxazepinones

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Abstract

The reactions of 2-carboxybenzaldehyde (1) with different 1,3- or 1,4-aminoalcohols (2a-i, 3a,b) were used to prepare partially saturated terra- and pentacyclic compounds containing a condensed 1,3-oxazino- or oxazepinoisoindolone moiety and one terminal saturated carbocycle. Isoindolo[2,1-a][3,1]benzoxazinones (4a-d, 6, 7), stereoisomeric isoindolo[l,2-b][2,4] benzoxazepinones (5a-c) and pentacyclic derivatives (4e-g) were obtained. The diastereomers 5a-c differ in the ring annelation or in the positions of the NCHO hydrogens and annelational hydrogens. The stereostructures of these compounds were elucidated by means of 1H and 13C NMR spectroscopy, including DNOE, DEPT and 2D-HSC measurements.

Original languageEnglish
Pages (from-to)29-36
Number of pages8
JournalJournal of Molecular Structure
Volume415
Issue number1-2
DOIs
Publication statusPublished - Aug 11 1997

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Keywords

  • NMR spectroscopy
  • Saturated isoindolo[2,1-a][3,1]benzoxazinones
  • Saturated isoindolo[2,3-b][2,4]benzoxazepiaones
  • Structure elucidation
  • Synthesis

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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