Pyridino-directed lithiation of anisylpyridines: new access to functional pyridylphenols

The lithiation of nine anisylpyridines has been studied. While usual reagents did not react or gave addition products on pyridine ring, the BuLi-LiDMAE (LiDNlAEz=Me2N(CH2)(2)OLi) superbase induced exclusive pyridino directed metallation. The usefulness of this new reaction allowed the efficient preparation of a range of alpha functional pyridylphenols. A successful subsequent cyclisation of an appropriate isomer into corresponding benzofuropyridine was also performed. (c) 2004 Elsevier Ltd. All rights reserved.