Reaction of 2‐dimethylaminomethylene‐1,3‐diones with dinucleophiles. V. Synthesis of 5‐acyl‐1,2‐dihydro‐2‐oxo‐3‐pyridinecarbonitriles and 1,2,5,6,7,8‐hexahydro‐2,5‐dioxo‐3‐quinolinecarboxamides

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Abstract
The reaction of open‐chain sym‐2‐dimethylaminomethylene‐1,3‐diones Ia‐d with sodium cyanoacetamide gave, generally in good yields, 6‐substituted 5‐acyl‐1,2‐dihydro‐2‐oxo‐3‐pyridinecarbonitriles IIa‐d, whereas cyclohexane sym‐2‐dimethylaminomethylene‐1,3‐diones Ie‐h afforded in general a mixture of 1,2,5,6,7,8‐hexahydro‐2,5‐dioxo‐3‐quinolinecarbonitriles and 5,6,7,8‐tetrahydro‐2,5‐dioxo‐2H‐1‐benzopyran‐3‐carboxamides, the latter being isolated in two cases. The reaction of Ie‐h with cyanoacetamide in refluxing anhydrous ethanol gave 1,2,5,6,7,8‐hexahydro‐2,5‐dioxo‐3‐quinolinecarboxamides IIIe‐h in excellent yields, whereas Ia‐d did not react with the exception of Ia which afforded in good yield 3‐pyridinecarboxamide IlIa. Other 3‐pyridine‐carboxamides were obtained by partial hydrolysis of nitriles IIb,d. 3‐Pyridine and 3‐quinoline carboxamides were hydrolyzed in satisfactory yields with hydrochloric acid to the corresponding carboxylic acids, which were decarboxylated in good yields to 5‐acyl‐2(1H)‐pyridinones and 7,8‐dihydro‐2,5(1H,6H)‐quinolinediones, respectively, by reflux in quinoline containing a catalytic amount of copper powder.

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