33259-10-8Relevant academic research and scientific papers
Rhodium-Catalyzed Asymmetric Hydrogenation of 3-Benzoylaminocoumarins for the Synthesis of Chiral 3-Amino Dihydrocoumarins
Xu, Yunnan,Liu, Delong,Deng, Yu,Zhou, Yi,Zhang, Wanbin
supporting information, p. 23602 - 23607 (2021/10/05)
An asymmetric hydrogenation of 3-benzoylaminocoumarins was achieved for the first time using our BridgePhos-Rh catalytic system, providing chiral 3-amino dihydrocoumarins in high yields (up to 98 %) and with excellent enantioselectivities (up to 99.7 % ee). The relationship between the enantioselectivities of the hydrogenations and the dihedral angles and the resulting π-π stacking effects of the BridgePhos-Rh complexes, which were determined by X-ray diffraction analysis, are discussed. The corresponding hydrogenated products allow for many transformations, providing several chiral skeletons with important physiological and pharmacological activities.
An efficient and facile synthesis of substituted 3-aminocoumarins under mw irradiation in dry media
Valizadeh, Hassan,Shockravi, Abbas
, p. 475 - 478 (2007/10/03)
A variety of 3-aminocoumarins were prepared by reaction of salicylaldehyde derivatives with benzoylglycine catalyzed by piperidine under microwave irradiation (MWI) and subsequent acid hydrolysis. The structure of products was proven by elemental analysis, IR, NMR and Mass spectra. These investigations will contribute to development of environmentally friendly and inexpensive processes in organic synthesis.
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.
