Two-Step Formation of Substituted Pyridines from Iodoenones

Abstract

A new access to substituted pyridines was developed from iodoenones. This two-step procedure involves a Sonogashira coupling with a free alkyne containing a nosylamide followed by a thiophenol treatment in basic conditions that triggers nosyl deprotection, a Michael–retro-Michael process, condensation, and isomerization in cascade to yield the heterocycle. This method enables the introduction of different substituents at several pyridine positions. This approach offers new synthetic opportunities to produce heterocycles present in many bioactive compounds.