Stereoselective functionalisation of pinopyridine with anisidines and o-phenylenediamine

Benzylic oxidation of pinopyridine with SeO₂ affords the corresponding keto derivative (71% yield) whose reductive amination with o- and p-anisidines proceeds stereoselectively to give 8R-amino derivatives; the reaction with o-phenylenediamine results in achiral pyridophenazine derivative possessing intense blue fluorescence at 441nm. Structures of o-anisidine derivative and substituted pyridophenazine have been characterized by X-ray crystallography.