Diels—Alder Reactions of N‐Acyl‐2‐alkyl(aryl)‐5‐vinyl‐2,3‐dihydro‐4‐pyridones.

Abstract

Fused pyridine derivatives R 0450Diels-Alder Reactions of N-Acyl-2-alkyl(aryl)-5-vinyl-2,3-dihydro-4-pyridones.-Diels-Alder cycloaddition of vinyldihydropyridones (I) with various dienophiles provides an efficient access towards octahydroquinolinones bearing diverse functionalities. The effect of C-2 substituents and of the replacement of C-4 carbonyl by hydroxyl functionality on the stereoselectivity of cycloaddition is studied. With certain dienophiles like benzo-or naphthoquinone and benzyne, the cycloaddition reaction is accompanied by aromatization due to extrusion of the carbamate functionality and pyridine ring opening. -(COMINS*, D. L.; KUETHE, J. T.; MILLER, T. M.; FEVRIER, F. C.; BROOKS, C. A.; J. Org. Chem. 70 (2005) 13, 5221-5234; Dep. Chem., N. C. State Univ., Raleigh, NC 27695, USA; Eng.) -Mischke 45-173