Synthesis of Unsymmetrically 4-Substituted 2,2'-Bipyridines

Article abstract of DOI:10.1016/0040-4039(94)02242-4

Pyridin-2-nitrile oxide was generated in situ and reacted with 2-substituted but-1-ene-4-ols to give 5-substituted 5-(2-hydroxyethyl)-3-(pyrid-2-yl)-Δ²-isoxazolines.The isoxazolines were reductively ring-opened with LiAlH4 to give 2-(3-substituted-1-amino-3,5-dihydroxypentyl)-pyridines, which were subjected to Dess-Martin oxidation with concomitant dehydration to give 4-substituted 2,2'-bipyridines.