The nucleophilic addition of enamines to a dicarboxy allene has provided the basis for an extremely valuable method of preparing highly substituted 2-pyridones.' (See Scheme I). It was of interest to study the extension of this reaction to include the synthesis of pyridones where C-5 (2, R=H) was unsubstituted. Such products are not directly available from the previous synthesis. A motivation for this study may be found in the synthesis of the anti-tumor alkaloid camptothecin (t)2 which is unsubstituted at C-14. Each of the enamines utilized in the previous study was conjugated with a carboxyl or carbonyl group (l, R=C02Et or COMe). The synthesis of the unsubstituted pyridones by this method would require the use of enamines in which R is hydrogen. The adducts of primary amines and carbonyl compoundsgenerally exist as the imine tautomers.3 However, the stability of the enamine tautomer is increased by Conjugation with an electron withdrawing group. Thus, in those compounds utilized in the previous study the enamine tautomers l would be expected to predominate. However, the compounds required Scheme I R' s