Studies on 1-Alkyl-2 (1H)-pyridone Derivatives. XIII. Syntheses of 5-endo-6-exo-Dicyano- and -Dimethoxycarbonyl-2-methyl-3-oxo-2-azabicyclo [2.2.2] oct-7-ene

Abstract

The Diels-Alder reaction of 1-methyl-2 (1H)-pyridone (I) and fumaronitrile was carried out and the structure of the adduct (II) thereby formed was determined as 5-endo-6-exo-dicyano-2-methyl-3-oxo-2-azabicyclo [2.2.2] oct-7-ene (IIa). IIa was obtained only in a low yield of 3% but the diester compound (Xa) with the same configuration was synthesized in a high yield of 88% by the epimerization of IX, obtained in a quantitative yield from the known VIII.