Synfacts 2010(10): 1116-1116  
DOI: 10.1055/s-0030-1258608
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Bicyclic Pyridones from 1,3-Butadienes

Contributor(s): Victor Snieckus, Emilie David
H. Yu, W. Jin, C. Sun, J. Chen, W. Du, S. He, Z. Yu*
Dalian Institute of Chemical Physics, Anshan Normal University and Shanghai Institute of Organic Chemistry, P. R. of China
Further Information

Publication History

Publication Date:
22 September 2010 (online)

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.