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

Harish R Talele, Ashutosh V Bedekar

Department of Chemistry, Faculty of Science, M.S. University of Baroda, Vadodara 390 002, India.

Organic & biomolecular chemistry 2012 Nov 21

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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.

Citation

Harish R Talele, Ashutosh V Bedekar. Synthesis of chiral bis-oxazines: a preliminary assessment of helical conformational framework. Organic & biomolecular chemistry. 2012 Nov 21;10(43):8579-82