title: Ruthenium-catalyzed cycloisomerization-6pi-cyclization: a novel route to pyridines.
abstract: [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.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Alicia C
authors.initials: AC
authors.lastname: Gutierrez
mesh_terms: 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
chemical_list: D000480:Alkynes; D020005:Propanols; D011725:Pyridines; D014867:Water; D012428:Ruthenium; C028255:propargyl alcohol