Methyl -2-benzoylamino-3-dimethylaminopropenoate

Methyl 2-benzoylamino-3-dimethylaminopropenoate reacts with barbituric acid or its 1,3-dimethyl derivative to give a pyranopyrimidine 118 (89JHC1273). 

Methyl 2-benzoylamino-3-dimethylaminopropenoate afforded with methyl 2-quinolylacetate a pyrido[l,2-a]quinoline derivative 133 (94JHC125). 

Benzoylamino-3-dimethylaminopropenoate reacts with methyl 2-pyridylacetate or 2-cyanomethylpyridine to give derivatives of the pyrido [l,2-fl]pyridine system. Alternatively, this ring system is also formed with ethyl A-methoxythiocarbonylglycine and TOF (Scheme 54) (94JHC125). 

The dimethylamino group in diethyl (2 R=Et) and dimethyl 1-dimethylamino-3-oxobut-l-ene-2,4-dicarboxylates (2 R=Me) can be exchanged very easily with nitrogen nucleophiles. With primary amines in methanol or ethanol under reflux for several hours, substitution of the dimethylamino group by an amine takes place followed by intramolecular nucleophilic attack of the amino group on the ester to afford 1-substituted 5-alkoxycarbonyl-4-hydroxypyridin-2(lH)-ones 56 in 16-93% yields (5cheme 21). In the reaction of 56 with methyl (Z)-2-benzoylamino-3-dimethylaminopropenoate (57), first the intermediate 58 was formed, which cyclized into 6-substituted 3-benzoylamino-8-ethoxycarbonyl-2H,5H-pyrido[4,3-li]pyran-2,5-diones (59). However, with 3-dimethyla-mino-2-(methoxycarbonyl)propenoate (60) intermediate 61 is formed... 

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