129207-39-2Relevant articles and documents
Methyl 2-Benzoylamino-3-dimethylaminopropenoate in the Synthesis of Fused Pyranones. The Synthesis of Derivatives of Tetrahydro-2H-1-benzopyran-2-one, Isomeric 2H-Naphtholpyran-2-one and 3H-Naphthopyran-3-one, Pyranobenzopyran-2,5-dione, and 7H-Pyranopyrimi...
Ornik, Brina,Cadez, Zvonko,Stanovnik, Branko,Tisler, Miha
, p. 1021 - 1024 (2007/10/02)
Methyl 2-benzoylamino-3-dimethylaminopropenoate (1) reacts with carbocyclic and heterocyclic 1,3-diketones or potential 1,3-diketones, such as 1,3-cyclohexanediones 2-4, and 4-hydroxy-2H-1-benzopyran-2-one derivative 17, in acetic acid to afford the corresponding 3-benzoylamino substituted 5-oxo-5,6,7,8-tetrahydro-2H-1-benzopyran-2-ones 5-7, and 2H,5H-pyranobenzopyran-2,5-dione derivative 18. 1-Naphthol (12) and 2-naphthol (13) produce the isomeric 2H-naphthopyran-2-one (14) and 3H-naphthopyran-3-one (15) derivatives, respectively.Ethyl cyclopentanone-2-carboxylate (8) and ethyl cyclohexanone-2-carboxylate (9) do not react under these conditions, while in polyphosphoric acid the cyclisation of the reagent 1 is taking place to give 4-dimethylaminomethylene-2-phenyl-5(4H)-oxazolone (10). 4,6-Dihydroxypyrimidine derivative 19 affords in acetic acid the noncyclized intermediate 20, which can be further transformed in polyphosphoric acid into 7H-pyranopyrimidin-7-one derivative 21.
