With Ammonia on o-Acylamino Acids

This type of reaction has not been well developed for esters, but the following examples are typical. 4-Acetamido-5-ethoxycarbonylpyridazine gave 

Huynh-Dinh, A. Kolb, C. Gouyette, J. Igolen, and S. Tran-Dinh, J. Org. Chem. 40, 2825 (1975). 

2- Methylbenz[3,l]oxazin-4-one (acetylanthranil) (177), set aside at 25°C with ammonia in benzene, was quantitatively converted to 2-methyl-quinazolin-4-one. Slow as this reaction was in dry, apolar solvents, it became immensely faster when the solvent was undried however, the product was then 2-acetamidobenzamide. Nevertheless, the reaction proceeded rapidly in pyridine, whether wet or dry, and the sole product was the quinazoline.331 

3- Amino-2-ethoxycarbonyl-4-methylpyrrole was converted to the di-methylaminomethyleneamino analog (178) with dimethylformamide and phosphoryl chloride. The product, set aside for 3 days with cold methanolic ammonia, gave 7-methylpyrrolo[3,2-rf]pyrimidin-4-one 179) in excellent yield.332 The corresponding reaction with methyl anthranilate gave quina-zolin-4-one quantitatively.333 

---