The cyclic α-keto
nitrone 3,4,5,6-tetrahydro-5,5-dimethyl-3-oxopyridine 1-oxide (III) when
treated with acetic anhydride and sulphuric acid gave in low yield a compound
(XI) having both enol lactone and vinylogous amide functional groups.
Hydrolysis and decarboxylation of compound
(XI) with aqueous potassium hydroxide gave a vinylogous amide (V), also
obtained by acid- or base-catalysed condensation of compound (III) with
isopropenyl acetate or acetone. Base-catalysed condensation of (III) with
methyl acetoacetate gave an ester (XVII) closely related to compound (V).