52703-21-6Relevant articles and documents
The synthesis of 4,7-disubstituted-2H-benzo[b][1,4]-oxazin-3(4H)-ones using Smiles rearrangement and their in vitro evaluation as platelet aggregation inhibitors
Xia, Shuai,Liu, Ji-Qiang,Wang, Xiu-Hua,Tian, Ye,Wang, Yu,Wang, Jing-Huan,Fang, Liang,Zuo, Hua
supporting information, p. 1479 - 1483 (2014/03/21)
A series of novel benzo[b][1,4]oxazin-3(4H)-one derivatives were synthesized as platelet aggregation inhibitors for structure-activity relationships (SAR) analysis. The synthetic pattern, involved Smiles rearrangement for the preparation of benzoxazine, was proven to be more efficient than the conventional methods. Biological evaluation demonstrated that among all the synthesized compounds, compound 9u (IC50 = 9.20 μM) exhibited the most potent inhibition activity compared with aspirin, the positive control (IC50 = 7.07 μM). Molecular docking revealed that these set of compounds could be the GPIIb/IIIa antagonist for that they could be situated in the binding site of GPIIb/IIIa receptor quite well.
Electrophilic Substitution with Rearrangement. Part 9. Dienones derived from Brominations of o-, m-, and p-Cresol
Brittain, Judith M.,Mare, Peter B. D. de la,Newman, Paul A.
, p. 32 - 41 (2007/10/02)
Regiospecific protodebromination of ring-substituted bromophenols derived from 2-, 3-, or 4-methylphenol can be effected by heating them with aqueous hydrogen iodide; the synthetic scope of this reaction has been explored.These di- and poly-bromophenols can generally be converted by further bromination in aqueous acetic acid into dienones , which have now been shown to have the 4-bromo-2,5-dienone rather than the 2-bromo-3,5-dienone structure.The rearrangemens of these dienones to ring-substituted polybromophenols by treatment with sulfuric acid have been investigated; where more than one product is formed, the regioselectivity differs from that prevailing in the corresponding direct bromination of the phenol with liquid bromine.The alternative rearrangements of these dienones in aprotic solvents with and without illumination have been compared with results obtained by reaction of methylphenols with bromine under the same conditions.Characteristic differences between the behaviours of 2-, 3-, and 4-methyl-substituted compounds reflect the specific reactions available to the particular dienones.