Observation on the DDQ Oxidation of 1-Acyldihidropyridines – A Synthetic Application.
Dedra J. Wallace, Andrew D. Gibb, Ian F. Connrell, Derek J. Kennedy, Karel M. J. Brands, Ulf H. Doling, Synthesis 2001, pp. 1784-1789.
A synthetic application of the rate difference in oxidation of regioisomerically substituted N-acyldihydropyridines is reported. This has allowed for isolation of pure 4-substituted pyridine isomers without the need for chromatography. Diels-Alder adducts between a dihydropyridine and DDQ were isolated and formation of novel hydroquinone ethers was also observed during some reactions.