Reaction of α,β-unsaturated carbodiimides with enamines leading to fused pyridine derivatives

The treatment of (5,5-dimethyl-3-oxo-1-cyclohexenyl)iminotriphenylphosphorane ( 2 ) with phenyl isocyanate ( 3a ) gave N-(5,5-dimethyl-3-oxo-1-cyclohexenyl)-N'-phenylcarbodiimide ( 4a ) in situ. The reaction of 4a with enamines proceeded smoothly to afford the pyridine ring formation with the elimination of amine. This means that 4a is regarded as a new class of 2-aza-1,3-butadiene. The scopes and limitation of this reaction are also discussed.