Ruthenium-Catalyzed Cycloisomerization−6π-Cyclization: A Novel Route to Pyridines
- 16 March 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (8), 1473-1476
- https://doi.org/10.1021/ol070163t
Abstract
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.Keywords
This publication has 11 references indexed in Scilit:
- Ruthenium-Catalyzed Cycloaddition of 1,6-Diynes and Nitriles under Mild Conditions: Role of the Coordinating Group of NitrilesChemistry – A European Journal, 2006
- Synthesis of Substituted Pyridine Derivatives via the Ruthenium-Catalyzed Cycloisomerization of 3-AzadienynesJournal of the American Chemical Society, 2006
- Selectivity in Nickel-Catalyzed Rearrangements of Cyclopropylen-ynesJournal of the American Chemical Society, 2005
- A Nickel-Catalyzed Route to PyridinesJournal of the American Chemical Society, 2005
- Ruthenium-Catalyzed Cycloisomerizations of DiynolsJournal of the American Chemical Society, 2005
- Construction of Pyridine Rings by Metal-Mediated [2 + 2 + 2] CycloadditionChemical Reviews, 2003
- An Unusual Ruthenium-Catalyzed Cycloisomerization of Alkynes and Propargyl AlcoholsJournal of the American Chemical Society, 2002
- Pyridines and their Benzo Derivatives: SynthesisPublished by Elsevier ,1996
- Thermal cyclization of cis-dienone-oximesTetrahedron Letters, 1972
- The Synthesis of 1-Acetyl-4-Isopropenyl-1-CyclopenteneJournal of the American Chemical Society, 1960