Methodology for regioselective synthesis of substituted pyridines via intramolecular oximino malonate hetero Diels-Alder reactions.
[structure] Various substituted pyridines can be prepared regioselectively by a sequence involving an intramolecular thermal or high-pressure Diels-Alder cycloaddition of an oximino malonate dienophile tethered to a dienic carboxylic acid, followed by mild aromatization of the resulting cycloadduct with cesium carbonate in DMF at room temperature.
Bland
D C
DC
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.
Raudenbush
B C
BC
Weinreb
S M
SM
D000215:Acylation; D002384:Catalysis; D002586:Cesium / Q000737:chemistry; D008314:Malonates / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014961:X-Ray Diffraction
D008314:Malonates; D011725:Pyridines; D002586:Cesium