Diels-Alder reactions of 5-vinyl-1-acyl-2-aryl-2,3-dihydro-4-pyridones: regio- and stereoselective synthesis of octahydroquinolines.
[reaction: see text] Readily available 5-vinyldihydropyridones 2 undergo Diels-Alder cyclization with various dienophiles to afford novel octahdroquinolines. The process is highly stereoselective and provides heterocyclic products containing synthetically useful functionality.
Kuethe
Jeffrey T
JT
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA.
Brooks
Clinton A
CA
Comins
Daniel L
DL
D015394:Molecular Structure; D011728:Pyridones / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011728:Pyridones; D011804:Quinolines