125812-05-7Relevant articles and documents
Solid phase synthesis of aminopropenones and aminopropenoates; efficient and versatile synthons for combinatorial synthesis of heterocycles
Westman, Jacob,Lundin, Ronny
, p. 1025 - 1030 (2007/10/03)
Simple and fast solid phase methods for the synthesis of heterocycles will be described. Two different three-step methods are presented. The first method includes esterifications of N-protected glycine derivatives to a solid support (Merrifield resin), formation of aminopropenoates and subsequent reaction with dinucleophiles. The second method includes methylamination of a Merrifield resin, formation of aminopropenones via in-situ formation of an active intermediate in a three-component reaction and finally treatment with dinucleophiles to form heterocycles. These procedures lead not only to the formation of heterocycles but also to simultaneous intramolecular cleavage of the products from the resin giving the product in pure form in the solution. In addition, the use of microwave dielectric heating enhanced the velocity of all reaction steps and was found to be a very efficient complement to the solid phase synthesis.
4-ETHOXYMETHYLENE-2-PHENYL-5(4H)-OXAZOLONE AS A SYNTHON FOR THE SYNTHESIS OF SOME 2H-PYRAN-2-ONES
Kepe, Vladimir,Kocevar, Marijan,Petric, Andrej,Polanc, Slovenko,Vercek, Bojan
, p. 843 - 849 (2007/10/02)
Treatment of 4-ethoxymethylene-2-phenyl-5(4H)-oxazolone with activated methylene compounds under acidic or basic conditions leads to 2H-pyran-2-ones and fused pyran-2-ones.On the other hand, methyl (3-benzoylamino-5-methoxycarbonyl-2-oxo-2H-pyran-6-yl)acetate (4) has also been prepared by a one-pot synthesis from dimethyl 1,3-acetone dicarboxylate, diethoxymethyl acetate, hippuric acid and acetic anhydride.
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.