Ruthenium-catalyzed cycloisomerization-6pi-cyclization: a novel route to pyridines.
[reaction: see text] Herein we report a method for the synthesis of substituted pyridines. The unsaturated ketones and aldehydes derived from the cycloisomerization of primary and secondary propargyl diynols in the presence of [CpRu(CH3CN)3]PF6 (1) are converted to 1-azatrienes which in turn undergo a subsequent electrocyclization-dehydration to provide pyridines with excellent regiocontrol.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
Gutierrez
Alicia C
AC
D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007536:Isomerism; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D000480:Alkynes; D020005:Propanols; D011725:Pyridines; D014867:Water; D012428:Ruthenium; C028255:propargyl alcohol