One-pot, benzylic amination reactions of azine N-oxides

Abstract

Nitrogen-containing aromatic heterocycles, found in many biologically active natural products and pharmaceutical drugs, constitute a highly important class of compounds in organic chemistry. In this context, areas such as the discoveries of new synthetic methods for both the synthesis and derivatization of nitrogen-containing heterocyclic compounds as well as for the introduction of nitrogen to a compound attract significant attention in the areas of organic and pharmaceutical chemistry. In this study, we have developed a new one-pot synthetic method for the benzylic amination of azine-N-oxides containing a methyl group at the 2-position. Following the optimization studies, the substrate scope of the developed reaction has been investigated in detail. The reaction tolerates quinoline and isoquinoline N-oxides with electron donating and withdrawing substituents as the electrophilic reaction partner as well as a broad range of nucleophilic primary, secondary and aromatic amines.