Synthesis of Bicyclic Pyridones from 1,3-Butadienes

Significance

Reported is an interesting palladium-catalyzed oxidative Heck coupling or C-H activation of α-oxoketene dithioacetals with terminal alkenes to produce functionalized 1,3-butadienes. A variety of 1,3-butadienes derived from acrylates, acrolein and styrenes were synthesized in low to good yields. Selected 1,3-butadienes were then converted into bicyclic pyridones in moderate to good yields by taking advantage of masked aldehyde and Michael reactivities in a simple reaction with diamines in ethanol.