Synthesis of chiral bis-oxazines: a preliminary assessment of helical conformational framework

Org Biomol Chem. 2012 Nov 21;10(43):8579-82. doi: 10.1039/c2ob26669e.

Abstract

A series of novel naphthalene attached bis-oxazines were synthesized and characterized. The bis-oxazines were studied by VT-NMR analysis to assess the possibility of conformational twist. The bis-oxazine prepared from (l)-methylvalinate show a helical conformational twist in the single crystal X-ray analysis. Three isomers of bis-oxazines were prepared from chiral α-methylbenzyl amines, the meso isomer showed small optical rotation probably indicating the helical conformational twist in the molecule.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Oxazines / chemical synthesis*
  • Oxazines / chemistry*

Substances

  • Amines
  • Oxazines