E. S. Vasilyev, A. M. Agafontsev, V. D. Kolesnik, Yu. V. Gatilov, A. V. Tkachev, “Stereoselective functionalisation of pinopyridine with anisidines and <i>o</i>-phenylenediamine”, Mendeleev Commun., 2011, Volume 21, Issue 5,Pages <nobr>253

This article is cited in 4 papers

Stereoselective functionalisation of pinopyridine with anisidines and o-phenylenediamine

E. S. Vasilyev^a, A. M. Agafontsev^a, V. D. Kolesnik^a, Yu. V. Gatilov^a, A. V. Tkachev^ab

^a N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation
^b Department of Natural Sciences, Novosibirsk State University, Novosibirsk, Russian Federation

Abstract: 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.

Language: English

DOI: 10.1016/j.mencom.2011.09.007